298891
(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone
99%
Synonym(s):
(4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone
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About This Item
Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
Molecular Weight:
177.20
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1211705
Product Name
(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone, 99%
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
SMILES string
C[C@H]1NC(=O)O[C@H]1c2ccccc2
InChI key
PPIBJOQGAJBQDF-VXNVDRBHSA-N
assay
99%
form
solid
optical activity
[α]18/D +168°, c = 2 in chloroform
optical purity
ee: 98% (GLC)
mp
121-123 °C (lit.)
Quality Level
Application
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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DIC-mediated coupling of carboxylic acids to (4R, 5S)-4-methyl-5-phenyl-2-oxazolidinone
Graham JM, et al.
Synthetic Communications, 30(7), 1221-1226 (2000)
Asymmetric synthesis of chiral organosulfur compounds using N-sulfinyloxazolidinones
Evans DA, et al.
Journal of the American Chemical Society, 114(15), 5977-5985 (1992)
The Journal of Organic Chemistry, 57, 1179-1179 (1992)
Tetrahedron Letters, 34, 2255-2255 (1993)
Tetrahedron, 48, 7527-7527 (1992)
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