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
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Quality Level
Assay
99%
form
solid
optical activity
[α]18/D +168°, c = 2 in chloroform
optical purity
ee: 98% (GLC)
mp
121-123 °C (lit.)
SMILES string
C[C@H]1NC(=O)O[C@H]1c2ccccc2
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
InChI key
PPIBJOQGAJBQDF-VXNVDRBHSA-N
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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The Journal of Organic Chemistry, 57, 1744-1744 (1992)
Tetrahedron, 48, 7527-7527 (1992)
Journal of the American Chemical Society, 115, 10742-10742 (1993)
DIC-mediated coupling of carboxylic acids to (4R, 5S)-4-methyl-5-phenyl-2-oxazolidinone
Synthetic Communications, 30(7), 1221-1226 (2000)
The Journal of Organic Chemistry, 57, 1179-1179 (1992)
Chromatograms
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