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

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

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

Product Name: (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
Formula Weight: 177.2
MOL File: 77943-39-6.mol

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

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)
pka: 12.35±0.60(Predicted)
form: Liquid
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)

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Safety

Hazard Codes: N
Safety Statements: 22-24/25
WGK Germany: 3
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 298891
Product name: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone
Purity: 99%
Packaging: 5g
Price: $103
Updated: 2024/03/01

TRC

Product number: M325455
Product name: (4R,5S)-4-Methyl-5-phenyloxazolidinone
Packaging: 100mg
Price: $165
Updated: 2021/12/16

AK Scientific

Product number: 2222AC
Product name: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone
Packaging: 5g
Price: $184
Updated: 2021/12/16

Matrix Scientific

Product number: 121366
Product name: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone
Purity: 98%
Packaging: 5g
Price: $192
Updated: 2021/12/16

SynQuest Laboratories

Product number: 4H56-1-572
Product name: (4R,5S)-4-Methyl-5-phenyl-2-oxazolidone
Purity: 97%
Packaging: 5G
Price: $125
Updated: 2021/12/16

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

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.

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%).

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

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View Lastest Price from (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE manufacturers

Henan Bao Enluo International TradeCo.，LTD

Product: (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE 77943-39-6
Price: US $150.00/kg
Min. Order: 1kg
Purity: 99.9%
Supply Ability: 10000MT
Release date: 2023-05-10

Henan Bao Enluo International TradeCo.，LTD

Product: 4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-2-one 77943-39-6
Price: US $30.00/kg
Min. Order: 1kg
Purity: 99.9%
Supply Ability: 10000MT
Release date: 2023-05-11

Zhuozhou Wenxi import and Export Co., Ltd

Product: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 77943-39-6
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

77943-39-6, (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONERelated Search:

(R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE (R)-4,5,5-TRIPHENYL-2-OXAZOLIDINONE (R)-(+)-5,5-DIPHENYL-4-BENZYL-2-OXAZOLIDINONE (4S,5R)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE Oxazole 2-Oxazolidone N-ACETYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE (2R,4S)-3-Benzoyl-4-methyl-2-phenyl-5-oxazolidinone N-CROTONYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE,N-CROTONYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE (R)-(+)-5,5-DIPHENYL-4-METHYL-2-OXAZOLIDINONE (4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone ,(4R,5R)-4-Methyl-5-phenyl-2-oxazolidinone (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone ,(4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone N-PROPIONYL-(4S,5R)-4-METHYL- 5-PHENYL-2-OXAZOLIDINONE (R)-(+)-5,5-DIPHENYL-4-ISOBUTYL-2-OXAZOLIDINONE (4R,5S)-(+)-CIS-4,5-DIPHENYL-2-OXAZOLIDINONE N-CROTONYL-(4R,5S)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE,N-CROTONYL-(4R,5S)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE (2S,4R)-3-Benzoyl-4-methyl-2-phenyl-5-oxazolidinone

(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

(4S,5S)-4-Methyl-5-phenyloxazolidin-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-phenyloxazolidin-2-one

(4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE USP/EP/BP

(4R,5S)-4-Methyl-5-phenyl-1,3-oxazolidin-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