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473278

Sigma-Aldrich

(S)-(−)-4-Oxo-2-azetidinecarboxylic acid

98%

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About This Item

Empirical Formula (Hill Notation):
C4H5NO3
CAS Number:
16404-94-7
Molecular Weight:
115.09
MDL number:
MFCD00799571
UNSPSC Code:
12352005
PubChem Substance ID:
24870891
NACRES:
NA.22

assay

98%

form

solid

optical activity

[α]20/D −46°, c = 1 in methanol

mp

99-102 °C (lit.)

SMILES string

OC(=O)[C@@H]1CC(=O)N1

InChI

1S/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)/t2-/m0/s1

InChI key

YSPMLLKKKHCTBN-REOHCLBHSA-N

General description

The crystals of (S)-(-)-4-oxo-2-azetidinecarboxylic acid are orthorhombic and belongs to P212121 space group.[1]

Application

Important building block for the synthesis of NMDA receptor antagonists,[2] 3-alkyl-L-aspartic acids,[3] and orally active β-lactam inhibitors.[4]

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 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
SHBD4841V
44096EM
22896DM
09713JH
09613JH

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Structures of (S)-(-)-4-oxo-2-azetidinecarboxylic acid and 3-azetidinecarboxylic acid from powder synchrotron diffraction data.
Mora AJ, et al.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 62(4), 606-611 (2006)
Hanessian, S. et al.
Synlett, 33-33 (1992)
Baldwin, J.E. et al.
Tetrahedron, 51, 11581-11581 (1995)
P E Finke et al.
Journal of medicinal chemistry, 38(13), 2449-2462 (1995-06-23)
The stereospecific synthesis of several 4-[(4-carboxyphenyl)oxy]- 3,3-dialkyl-1-[[(1-phenylalkyl)-amino]carbonyl]azetidin-2-on es 3 is described in which the C-3 alkyl groups were varied from methyl to butyl as well as allyl, benzyl and methoxymethyl. The structure-activity relations for these compounds are discussed in terms

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