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Boceprevir InterMediates

Boceprevir InterMediates Structure
Boceprevir InterMediates structure
CAS No.
565456-77-1
Chemical Name:
Boceprevir InterMediates
Synonyms
Methyl (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate;Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;(1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;(1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE;(1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate;(1R,2S,5S)—6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride;tert-butyl ((S)-1-cyano-2-((S)-2-oxopyrrolidin-3-yl)ethyl)carbamate;(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride;Boceprevir INT 1;Paxlovid Impurity 2
CBNumber:
CB12466508
Molecular Formula:
C9H16ClNO2
Molecular Weight:
205.68
MDL Number:
MFCD11865137
MOL File:
565456-77-1.mol
Last updated:2023-10-08 21:24:08
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Boceprevir InterMediates Properties

storage temp. Inert atmosphere,Room Temperature
form solid
color Pale yellow
InChI InChI=1/C9H15NO2.ClH/c1-9(2)5-4-10-7(6(5)9)8(11)12-3;/h5-7,10H,4H2,1-3H3;1H/t5-,6-,7-;/s3
InChIKey FKVUDBWXNAFSPB-AUBOPKACNA-N
SMILES C([C@H]1NC[C@@H]2C(C)(C)[C@H]12)(=O)OC.Cl |&1:1,4,8,r|
FDA UNII 33ARM3Z735

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H332-H335-H319-H315
Precautionary statements  P261-P305+P351+P338
HS Code  2933998090

Boceprevir InterMediates price More Price(20)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC M342865 (1R,2S,5S)-Methyl6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylatehydrochloride 565456-77-1 50mg $75 2021-12-16 Buy
TRC M342865 (1R,2S,5S)-Methyl6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylatehydrochloride 565456-77-1 10mg $60 2021-12-16 Buy
Biosynth Carbosynth FD22289 (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester hydrochloride 565456-77-1 500mg $70 2021-12-16 Buy
American Custom Chemicals Corporation CCH0007548 (1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE 95.00% 565456-77-1 0.5MG $825 2021-12-16 Buy
Synthonix M14329 Methyl(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylatehydrochloride 95+% 565456-77-1 10g $910 2021-12-16 Buy
Product number Packaging Price Buy
M342865 50mg $75 Buy
M342865 10mg $60 Buy
FD22289 500mg $70 Buy
CCH0007548 0.5MG $825 Buy
M14329 10g $910 Buy

Boceprevir InterMediates Chemical Properties,Uses,Production

Uses

(1R, 2S, 5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate methyl ester hydrochloride is the cost in the side chain synthesis of boceprevir the highest key intermediate.

Uses

(1S,2S,5R)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride is an azabicyclohexane derivative used in the preparation of hepatitis C virus (HCV) NS3 serine protease inhibitor.

General Description

Boceprevir is a peptidomimetic protease inhibitor with four moieties, P1–P3 and a Cap, where P1 is a racemic β-aminoamide, P2 is a chiral dimethylcyclopropylproline analog, P3 is (S)-tert-leucine, and Cap is a tert-butylcarbamoyl group. The 3-azabicyclo[3.1.0]hexane structure of P2 adopts a constrained conformation, so that the gem-dimethyl group has a fixed angle with respect to the bicyclic ring structure. The incorporation of the 3-azabicyclo[3.1.0]hexane moiety results in a 1000-fold increase in NS3 protease binding over proline in a pentapeptide scaffold. When boceprevir binds to the NS3 protease, the P2 moiety interacts with four amino acid residues at the active site. The starting material for the P2 moiety is the HCl salt of the dimethylcyclopropylproline methyl ester 2. For medicinal chemistry studies, it was prepared by cyclopropanation of a Δ3-pyrroline derivative of pyroglutamic acid.
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Synthesis

1.png
The amine oxidation was carried out in a RC-1 Process Development Workstation (Mettler Toledo) equipped with pH feedback control and a gas induction impeller. A solution of 2.5 g MAON401(Codexis), 7.0 g catalase (Novozyme), and 0.1 g Antifoam 204 in 255 mL phosphate buffer (pH 7.0, 20 mM) was charged to the reactor. The temperature was set at 25°C, and 3 N NaOH was added to adjust the pH to 7.4. Pure oxygen (4 psig, or 207 mmHg) was applied to the enzyme solution prior to substrate addition. The substrate solution was prepared by dissolving 50 g NaHSO3 (0.45 mol) and 40 g 6 (0.36 mol) in 240 mL water. The substrate solution was charged to the enzyme solution over 19 h while maintaining the pH at 7.4 by titration of 3 N NaOH. By the end of the addition, 56.5 g of 3 N NaOH (0.15 mol) had been added to the reaction mixture, and conversion was 96.4%. For cyanation, CPME (240 mL) was added to the stream (compound 5 and 7) from enzymatic step. The solution was chilled to 10°C. A solution of NaCN in 70 mL water (22.9 g, 0.45 mol) was added over 0.5 h. The cyanation reached > 98% conversion after additional 0.5 h at 10°C. Significant protein precipitation took place when cyanide was added. The insoluble was removed by filtration through celite. After phase split, the aqueous phase was back extracted with 100 mL CPME. In methanolysis step, the CPME solution of 8 was added to HCl in MeOH (260 mL, [HCl] ≥ 6 N) at 5-10°C over 1 h. The solution was heated to 50°C and agitated for 4 h to complete the conversion. For product isolation, the volume was reduced to 160 mL by evaporation, followed by extraction under basic condition to give a solution of 9 in MTBE (375 mL). In the final step, the product was isolated by crystallization after forming the HCl salt. The MTBE solution was added to HCl in a mixture of 60 mL iPrOH and 240 mL MTBE at 0°C. The solution was seeded to crystallize for 5 h at -10°C. After solid isolation and drying under vacuum, 41.2 g (0.20 mol, 56% overall yield) of 2 was obtained in >98.5% purity and >99.9% e.e.

Boceprevir InterMediates Preparation Products And Raw materials

Raw materials

Preparation Products

Boceprevir InterMediates Suppliers

Global( 331)Suppliers
Supplier Tel Email Country ProdList Advantage
weifang runzhong fine chemical co., ltd
536-7868377 +8618653686003 sq@runzhongchem.com China 187 58
Shanghai QiXin New Materials Technology Co.,Ltd
+8615116235351 derrickguo@sh-qixin.cn China 16 58
Wuhan Topule Biopharmaceutical Co., Ltd
+8618327326525 masar@topule.com China 8474 58
Aceschem Inc.
+1-817863-6948 +1-（817）863-6948 sales@aceschem.com United States 19639 58
Hebei Yanxi Chemical Co., Ltd. 		+8617531190177 peter@yan-xi.com China 5999 58
Hangzhou ICH Biofarm Co., Ltd 		+undefined8613073685410 sales@ichemie.com China 985 58
Anhui Ruihan Technology Co., Ltd 		+8617756083858 daisy@anhuiruihan.com China 994 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21689 55
Hangzhou FandaChem Co.,Ltd. 		008657128800458; +8615858145714 fandachem@gmail.com China 9341 55
Supplier Advantage
weifang runzhong fine chemical co., ltd
58
Shanghai QiXin New Materials Technology Co.,Ltd
58
Wuhan Topule Biopharmaceutical Co., Ltd
58
Aceschem Inc.
58
Hebei Yanxi Chemical Co., Ltd. 		58
Hangzhou ICH Biofarm Co., Ltd 		58
Anhui Ruihan Technology Co., Ltd 		58
Capot Chemical Co.,Ltd. 		60
Henan Tianfu Chemical Co.,Ltd. 		55
Hangzhou FandaChem Co.,Ltd. 		55

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View Lastest Price from Boceprevir InterMediates manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE pictures 2024-04-23 (1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
565456-77-1
 US $3150.00 / kg/USD 3150kg/USD 99% 10TONE Great Innovation (Shanghai) Pharma Co., Ltd.,
(1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochloride pictures 2024-03-28 (1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochloride
565456-77-1
 US $0.00 / kg 25kg 98% Inquiry PNP Biotech Co. Ltd
(1r,2s,5s)-6,6-Dimethyl-3-Aza-Bicyclo[3.1.0]Hexane-2-Carboxylic Acid Methyl Ester Hydrochloride pictures 2023-11-13 (1r,2s,5s)-6,6-Dimethyl-3-Aza-Bicyclo[3.1.0]Hexane-2-Carboxylic Acid Methyl Ester Hydrochloride
565456-77-1
 US $0.00 / Kg/Bag 1Kg/Bag 98% 1 ton Wuhan Boye Science And Technology Development Co., Ltd.

565456-77-1(Boceprevir InterMediates)Related Search:

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Boceprevir InterMediates (1S,2S,5R)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, hydrochloride, (1R,2S,5S)- 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-diMethyl-,Methylester,hydrochloride(1:1),(1R,2S,5S)- (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester HCl 1.3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-dimethyl-, methyl ester, hydrochloride(1R,2S,5S) (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate acid Methyl ester hydrochloridee (1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-... (1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochlorid (1R,2S,5S)-Methyl 6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate HCl PF-07321332-002 Paxlovid Int. (1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORID PF-07321332 intermediate 6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE 5S)-6 (1R,2S,5S)—6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride (1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, (Hydrochloride), (1R,2S,5S)- (9CI) (1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate Boceprevir INT 1 (1R,2S,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE Nirmatrelvir Intermediate Nirmatrelvir intermediate 565456-77-1 Paxlovid Impurity 2 (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride tert-butyl ((S)-1-cyano-2-((S)-2-oxopyrrolidin-3-yl)ethyl)carbamate Methyl (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate (1R.28,5S)-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2- CARBOXYLICACID METHYL ESTER HYDRoCHLORIDE Paxlovid Intermediate 2 (1R,2S,5S)-6,6-dimethyl-3-aza-bicylo[3.1]hexane-2-carboxylic acid methyl ester hydrochloride 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-dimethyl-, methyl ester, hydrochloride (1:1), (1R,2S,5S)- (ACI) Paxlovid Interediate Intermediate of Boprevir PF-07321332 Impurity 1 6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester hydrochloride Nirmatrelvir Impurity 10 HCl Methyl (1S,2S,5R)-1,5,6,6-tetramethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate Nirmatrelvir Impurity 29 HCl 565456-77-1 Boceprevir intermediate Chiral Reagents Heterocycles Intermediates & Fine Chemicals Pharmaceuticals 565456-77-1