ChemicalBook >> CAS DataBase List >>(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

CAS No.
77943-39-6
Chemical Name:
(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE
Synonyms
(4R,5S)-4-Methyl-5-phenyloxazolidin-2-one;(4S,5S)-4-Methyl-5-phenyloxazolidin-2-one;TB-2039;4-methyl-5-phenyl-2-oxazolidinone;5β-Phenyl-4β-methyloxazolidine-2-one;4α-Methyl-5α-phenyloxazolidine-2-one;4-Methyl-5-phenyl-1,3-oxazolidin-2-one;(4R-5S)-4-Methyl-5-Phenyl-2-Oxazocidin;(4R,5S)-4-Methyl-5-phenyl-2-oxazolidone;(4R,5S)-4-Methyl-4-phenyl-2-oxazolidone
CBNumber:
CB5321737
Molecular Formula:
C10H11NO2
Molecular Weight:
177.2
MDL Number:
MFCD00010845
MOL File:
77943-39-6.mol
MSDS File:
SDS
Last updated:2023-05-25 10:25:51

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Properties

Melting point 121-123 °C(lit.)
Boiling point 309.12°C (rough estimate)
Density 1.1607 (rough estimate)
refractive index 1.5168 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Liquid
pka 12.35±0.60(Predicted)
color Clear colorless to yellow-brown, may darken in storage
optical activity [α]18/D +168°, c = 2 in chloroform
BRN 1211705
InChI InChI=1S/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
InChIKey PPIBJOQGAJBQDF-VXNVDRBHSA-N
SMILES O1[C@@H](C2=CC=CC=C2)[C@@H](C)NC1=O
CAS DataBase Reference 77943-39-6(CAS DataBase Reference)
FDA UNII 05339K0T1Y

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  N
Safety Statements  22-24/25
WGK Germany  3
HS Code  29349990

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE price More Price(19)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 298891 (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 99% 77943-39-6 5g $103 2024-03-01 Buy
TRC M325455 (4R,5S)-4-Methyl-5-phenyloxazolidinone 77943-39-6 100mg $165 2021-12-16 Buy
AK Scientific 2222AC (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 77943-39-6 5g $184 2021-12-16 Buy
Matrix Scientific 121366 (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 98% 77943-39-6 5g $192 2021-12-16 Buy
SynQuest Laboratories 4H56-1-572 (4R,5S)-4-Methyl-5-phenyl-2-oxazolidone 97% 77943-39-6 5G $125 2021-12-16 Buy
Product number Packaging Price Buy
298891 5g $103 Buy
M325455 100mg $165 Buy
2222AC 5g $184 Buy
121366 5g $192 Buy
4H56-1-572 5G $125 Buy

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Chemical Properties,Uses,Production

Chemical Properties

white to light yellow crystal powde

Uses

Evan′s chiral auxiliary (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone reacts with carboxylic acids to produce corresponding acyl derivatives in the presence of a diisopropylcarbodiimide reagent. It can also employed in the preparation of N-sulfinyloxazolidinone reagent (chiral sulfinyl transfer reagent), which reacts with nucleophiles such as Grignard reagents, enolates, and metalated amides to produce the chiral sulfoxides, sulfinate esters, and sulfonamides.

Uses

(4R,5S)-4-Methyl-5-phenyloxazolidinone is used as effective chiral auxiliary for conjugate addition asymmetric synthesis of (-)-aplysillamide B.

Preparation

To a solution of (1S,2R)-norephedrine (40 g, 0.26 mol) in toluene (400 mL) was added diethyl carbonate (37 mL, 0.32 mol). The mixture was heated to reflux (under Ar) while 40 mL of solvent was removed through the use of a Dean–Stark apparatus. The mixture was allowed to cool for 20 min, and then sodium methoxide (1 g) was added. Upon reheating, an EtOH/toluene azeotropic mixture was removed at 75–77 °C. After 3 h, the reaction was complete and the temperature of the mixture had increased to 125 °C. The mixture was left to stand at room temperature for 16 h, whereupon (4R,5S)-4-methyl-5-phenyloxazolidin-2-one (40.6 g) crystallized and could be collected. The solvent was removed from the filtrate in vacuo and the residue was redissolved in EtOAc (250 mL). This solution was washed with brine (50 mL) and a precipitate was removed by filtration. The solvent was then removed in vacuo and toluene (50 mL) was added to the residue. Removal of the toluene by distillation yielded oily crystals of the oxazolidinone, which were washed with Et2O to afford 4.5 g (total 45 g, 97%).

Definition

ChEBI: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone is a member of benzenes.

Preparation

A mechanically stirred mixture of (1S,2R)-norephedrine 710 (151 g, 1.00 mol) ([α]589 =+ 33.4 (c= 7, water)), as the hydrochloride salt, diphenyl carbonate (236 g, 1.10 mol), and anhydrous potassium carbonate (152 g, 1.10 mol) was heated at 110 °C for 4–6 h. The resultant mixture was then cooled to <60 °C. Excess diphenyl carbonate was hydrolyzed by adding methanol (600 mL) and heating the mixture under reflux for 0.5 h. Sufficient water (400–600 mL) was then added to dissolve the potassium carbonate. Methanol was removed in vacuo. The product and phenol were extracted into dichloromethane (3 × 1 L). The combined extracts were washed with 2 m aqueous sodium hydroxide (3 × 1 L) to remove the phenol, 1 m aqueous hydrochloric acid (1 × 1 L), and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give 195 g (110% mass balance) of a light-yellow solid. Recrystallization from toluene (600 mL) afforded 145–165 g (82–93%) of oxazolidinone 711 as a white crystalline solid.
the preparation of (4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone

Synthesis Reference(s)

Tetrahedron Letters, 40, p. 6059, 1999 DOI: 10.1016/S0040-4039(99)01256-3

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 140)Suppliers
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Henan Bao Enluo International TradeCo.,LTD
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Dayang Chem (Hangzhou) Co.,Ltd.
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View Lastest Price from (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE pictures 2023-05-27 (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE
77943-39-6
US $150.00 / kg 1kg 99.9% 10000MT Henan Bao Enluo International TradeCo.,LTD
4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one pictures 2023-05-27 4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one
77943-39-6
US $30.00 / kg 1kg 99.9% 10000MT Henan Bao Enluo International TradeCo.,LTD
(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone pictures 2021-07-02 (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone
77943-39-6
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 99% 4-Methyl-5-phenyl-1,3-oxazolidin-2-one (4R,5S)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-4-Methyl-5-phenyl-2-oxazolidone (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLID -INONE, 99% (99% EE/GLC) (4R,5S)-4-METHYL-5-PHENYL-2-OXAZOLIDI DI NONE 2-Oxazolidinone, 4-methyl-5-phenyl-, (4R,5S)- 4-methyl-5-phenyl-2-oxazolidinone (4S)-4β-Methyl-5α-phenyloxazolidine-2-one 5β-Phenyl-4β-methyloxazolidine-2-one (4R)-4α-Methyl-5α-phenyloxazolidin-2-one 4α-Methyl-5α-phenyloxazolidine-2-one (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone,99% (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidine (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone ,98% (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE USP/EP/BP (4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one (4S,5S)-4-Methyl-5-phenyloxazolidin-2-one (4R,5S)-4-Methyl-5-phenyloxazolidin-2-one TB-2039 (4R-5S)-4-Methyl-5-Phenyl-2-Oxazocidin (4R,5S)-4-Methyl-4-phenyl-2-oxazolidone 77943-39-6 Chiral Auxiliaries Asymmetric Synthesis Oxazolidinone Derivatives chiral Peptide