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298891

Sigma-Aldrich

(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:
77943-39-6
Molecular Weight:
177.20
Beilstein/REAXYS Number:
1211705
MDL number:
MFCD00010845
UNSPSC Code:
12352005
PubChem Substance ID:
24858003
NACRES:
NA.22

Key Documents

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Quality Level

100

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

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This Item
294640658405668540
(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone 99%

Sigma-Aldrich

298891

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

(S)-4-Benzyl-2-oxazolidinone 99%

Sigma-Aldrich

294640

(S)-4-Benzyl-2-oxazolidinone

(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone 97%

Sigma-Aldrich

658405

(S)-4-(4-Aminobenzyl)-2(1H)-oxazolidinone

(2S,5S)-(–)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone 95%

Sigma-Aldrich

668540

(2S,5S)-(–)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone

assay

99%

assay

99%

assay

97%

assay

95%

form

solid

form

solid

form

solid

form

-

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

mp

121-123 °C (lit.)

mp

86-88 °C (lit.)

mp

107-111 °C

mp

-

optical activity

[α]18/D +168°, c = 2 in chloroform

optical activity

[α]20/D −63°, c = 1 in chloroform

optical activity

-

optical activity

-

optical purity

ee: 98% (GLC)

optical purity

ee: 99% (HPLC)

optical purity

-

optical purity

-

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.[1] 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.[2]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000499110
0000499110
0000484186
0000484186
MKBV3698V

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Tetrahedron, 48, 7527-7527 (1992)
The Journal of Organic Chemistry, 57, 1744-1744 (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
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)
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