ChemicalBook >> CAS DataBase List >>2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate structure

CAS No.: 170098-38-1

Chemical Name:: 2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate

Synonyms: Entereg;Alvimopan 2H2O;Alvimopan hydrate;Ly 246736 dihydrate;Alvimopan dihydrate;Ly 246736 2-hydrate;ADL 8-2698 dihydrate;156053-89-3 (Anhydrous);Alvimopan dihydrate, >=99%;Alvimopan Dihydrate Labeled d7

CBNumber:: CB21261077

Molecular Formula:: C25H36N2O6

Molecular Weight:: 460.57

MDL Number:: MFCD00927248

MOL File:: 170098-38-1.mol

MSDS File:: SDS

Last updated:2023-05-18 11:31:20

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2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate Properties

Melting point	210-213°
alpha	D25 +51.8° (c = 1.0 in DMSO)
storage temp.	2-8°C
solubility	Soluble in DMSO
form	Powder
FDA UNII	677C126AET
NCI Drug Dictionary	Entereg

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H332-H335
Precautionary statements	P261-P280-P305+P351+P338

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate price

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
ChemScene	CS-1540	Alvimopan(dihydrate) 98.70%	170098-38-1	5mg	$110	2021-12-16	Buy
ApexBio Technology	A3163	Alvimopandihydrate	170098-38-1	5mg	$159	2021-12-16	Buy
ChemScene	CS-1540	Alvimopan(dihydrate) 98.70%	170098-38-1	10mg	$160	2021-12-16	Buy
ApexBio Technology	A3163	Alvimopandihydrate	170098-38-1	10mg	$252	2021-12-16	Buy
ChemScene	CS-1540	Alvimopan(dihydrate) 98.70%	170098-38-1	50mg	$480	2021-12-16	Buy

Product number	Packaging	Price	Buy
CS-1540	5mg	$110	Buy
A3163	5mg	$159	Buy
CS-1540	10mg	$160	Buy
A3163	10mg	$252	Buy
CS-1540	50mg	$480	Buy

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate Chemical Properties,Uses,Production

Description

Alvimopan is a μ-opioid receptor antagonist approved in the U.S. in May 2008 for the treatment of post-operative ileus (POI) – a temporary dysfunction of the gastrointestines. Alvimopan does not penetrate the central nervous system (CNS) and acts as a peripheral antagonist. The molecule inhibits the negative effects of opioids on the gastrointestinal (GI) system without inhibiting the desired analgesic effects of CNS penetrant opioids.

Uses

Treatment of opioid-induced bowel dysfunction, opioidinduced nausea and vomiting, postoperative ileus, idiopathic constipation, and irritable bowel syndrome (peripherally restricted mu opioid receptor antagonist).

Synthesis

Several synthetic routes have been disclosed, and the process route is described in the scheme. This route was performed on kilogram scale and no yields were reported beyond the generation of compound 8. 3-Bromophenol 1 was treated with isopropyl bromide and potassium carbonate at 60-65 ??C for 16 h to give 3-isopropyoxy bromobenzene 2. Bromide 2 was added to a suspension of Mg turnings in THF at 40-60 ??C generating the corresponding Grignard reagent to which a solution of 1,3-dimethylpiperidone 3 in THF was added as four separate fractions over a period of 2 h. Upon completion, the reaction mixture was quenched with aqueous ammonium chloride, the product was extracted into heptane and crystallized out of solution and was isolated by filtration to provide a cis-(?à) enriched mixture of piperidone alcohol 4 in 97% purity. This mixture was recrystallized from heptane to afford exclusively the cis-(?à) piperidone 4 in 97% purity and 66% yield. Piperidone alcohol 4 was treated with ethylchloroformate and triethyl amine at 0??C and warmed to room temperature over 3 h. The resulting ethylcarbonate was resolved via classical resolution with (+)-di-p-toluyl-Dtartaric acid and then recrystallized from ethanol to give 5 in 99% purity and 99.5% ee. The conversion of 5 to 3,4-trans dimethyl piperidine 8 followed the sequence described by Werner, et. al. as no experimental was disclosed in the process patent for this sequence. The (+)-DTTA salt 5 was treated with sodium hydroxide to liberate the free base which then underwent thermal elimination of the carbonate at 190 ??C in decalin to give the desired trisubstituted olefin 6 in 92% yield. Treatment of piperidine 6 with n-BuLi followed by addition of dimethyl sulfate at -50 ??C gave the desired 3,4-trans-dimethyl enamine 7. Due to the reactivity of the dimethyl sulfate, only one equivalent was used and the reaction had to be quenched into aqueous ammonium hydroxide to avoid N-methylation. The crude enamine 7 was reduced with sodium borohydride and purified by crystallization with (+)-DTTA, giving (+)-DTTA salt 8 in 65% overall yield from 5. Additionally, the crystallization provided 8 with less than 1% impurities and 98.8% ee. The free base of 8 was liberated upon treatment with sodium hydroxide and reacted with phenyl chloroformate at 80-85 ??C, to effectively demethylate the nitrogen. The resulting crude phenylcarbamate 9 was refluxed in HBr/acetic acid for 18 h to simultaneously cleave the isopropyl ether and carbamate protecting groups to give the aminophenol 10, which was precipitated out of solution and collected by filtration. Amine 10 was then treated with methylacrylate (11) in THF at 40-45 ??C for 18-19 h to give the intermediate 12, which was transferred directly into a solution of LDA. A solution of benzyl bromide in THF was added to the enolate of 12 at -20 ??C and upon complete benzylation, 13 was isolated as its HCl salt. Ester 13 was hydrolyzed with sodium hydroxide to give 14, which was coupled to glycine ethyl ester hydrochloride 15 in the presence of DCC, HOBT and triethylamine in THF providing crude ethyl ester 16. Finally, ester 16 was hydrolyzed with sodium hydroxide to give alvimopan (I), which was purified by crystallization from the reaction mixture in 99.2% purity and 99% ee.

Synthesis_170098-38-1

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate Preparation Products And Raw materials

Raw materials

Preparation Products

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate Suppliers

Global( 97)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	15928	58
Hangzhou Cyanochem Co., Ltd.	+86 17788583750	sales@cyanochem.com	CHINA	283	58
Xiamen AmoyChem Co., Ltd	+86-592-6051114 +8618959220845	sales@amoychem.com	China	6387	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	47465	58
career henan chemical co	+86-0371-86658258 15093356674;	factory@coreychem.com	China	29826	58
Hubei Ipure Biology Co., Ltd	+8613367258412	ada@ipurechemical.com	China	10326	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	86-571-88216897,88216896 13588875226	sales@hzclap.com	CHINA	6313	58
Shanxi Xuanran Import and Export Trade Co., Ltd.	+8617735180244	mike_yan@xuanranglobal.com	CHINA	4022	58
AFINE CHEMICALS LIMITED	0571-85134551	info@afinechem.com	CHINA	15377	58
Finetech Industry Limited	+86-27-87465837 +8618971612321	info@finetechnology-ind.com	China	9702	58

Supplier	Advantage
Shanghai Daken Advanced Materials Co.,Ltd	58
Hangzhou Cyanochem Co., Ltd.	58
Xiamen AmoyChem Co., Ltd	58
CONIER CHEM AND PHARMA LIMITED	58
career henan chemical co	58
Hubei Ipure Biology Co., Ltd	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	58
Shanxi Xuanran Import and Export Trade Co., Ltd.	58
AFINE CHEMICALS LIMITED	58
Finetech Industry Limited	58

View Lastest Price from 2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate manufacturers

Image	Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
	2020-02-14	2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate 170098-38-1	US $7.00 / KG	1KG	99%	100KG	Career Henan Chemical Co

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate
170098-38-1
US $7.00 / KG
99%
Career Henan Chemical Co

170098-38-1(2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate)Related Search:

AlviMopan (Monohydrate)

2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperi dyl]propanoyl]amino]acetic acid dihydrate [[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl]-3-phenylpropanoyl]amino]acetic acid dehydrate (((2S)-2-(((3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)methyl)-3-phenylpropanoyl)amino)acetic acid dihydrate 156053-89-3 (Anhydrous) Alvimopan hydrate Entereg Glycine, N-((2S)-2-(((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl)methyl)-1-oxo-3-phenylpropyl)-, dihydrate Glycine, N-(2-((4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl)methyl)-1-oxo-3-phenylpropyl)-,dihydrate, (3R-(1(S*),3-alpha,4-alpha))- Ly 246736 dihydrate AlviMopan(ADL-8-2698,LY-246736) ADL 8-2698 dihydrate Glycine,N-[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-diMethyl-1-piperidinyl]Methyl]-1-oxo-3-phenylpropyl]-,hydrate (1:2) Alvimopan dihydrate, >=99% Alvimopan 2H2O Alvimopan dihydrate N-[(2S)-2-[[(3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]glycine dihydrate N-{(2S)-2-Benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]propanoyl}glycine 2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl]amino]acetic acid,dihydrate LY 246736 DIHYDRATE; ADL 8-2698 DIHYDRATE Alvimopan dihydrate (LY246736 dihydrate) Ly 246736 2-hydrate 2-((S)-2-Benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)acetic acid dihydrate Alvimopandihydrate/ADL8-2698dihydrate Alvimopan Dihydrate Labeled d7 170098-38-1 C25H32N2O42H2O C25H36N2O6 API