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

Belgium 1 Canada 2 China 84 France 2 Germany 4 India 10 Japan 1 Switzerland 2 United Kingdom 5 United States 23 Global 134
Ark Pharm, Inc.
Tel
847-367-3680
Fax
847-367-3681
Email
sales@arkpharminc.com
Country
United States
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Accela ChemBio Inc.
Tel
+1(858) 699-3322
Fax
+1(858) 876-1948
Email
marketing@accelachem.com
Country
United States
ProdList
6027
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Accela ChemBio Inc.
Tel
(+1)-858-699-3322
Fax
(+1)-858-876-1948
Email
info@accelachem.com
Country
United States
ProdList
19965
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58
Alchem Pharmtech,Inc.
Tel
8485655694
Email
sales@alchempharmtech.com
Country
United States
ProdList
63711
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58
Aladdin Scientific
Tel
+1-833-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
52927
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58
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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