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391344

Sigma-Aldrich

(S)-(+)-2-Oxo-4-phenyl-3-oxazolidineacetic acid

98%

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About This Item

Empirical Formula (Hill Notation):
C11H11NO4
CAS Number:
99333-54-7
Molecular Weight:
221.21
MDL number:
MFCD00192376
UNSPSC Code:
12352005
PubChem Substance ID:
24864372
NACRES:
NA.22

assay

98%

optical activity

[α]28/D +165°, c = 2 in chloroform

mp

103-105 °C (lit.)

SMILES string

OC(=O)CN1[C@H](COC1=O)c2ccccc2

InChI

1S/C11H11NO4/c13-10(14)6-12-9(7-16-11(12)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)/t9-/m1/s1

Inchi Key

PUKMRNJLFMISMT-SECBINFHSA-N

Application

The chiral ketene derived from this product leads to chiral β-lactams via the Staudinger reaction.[1] This strategy has been extended to prepare unnatural dipeptides.[2]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
09516HJ
14724CD
04215MC
14911LA
15219CZ

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Tetrahedron Letters, 26, 3783-3783 (1985)
Journal of the American Chemical Society, 112, 770-770 (1990)

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