473278
(S)-(−)-4-Oxo-2-azetidinecarboxylic acid
98%
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About This Item
Empirical Formula (Hill Notation):
C4H5NO3
CAS Number:
Molecular Weight:
115.09
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
InChI
1S/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)/t2-/m0/s1
SMILES string
OC(=O)[C@@H]1CC(=O)N1
InChI key
YSPMLLKKKHCTBN-REOHCLBHSA-N
assay
98%
form
solid
optical activity
[α]20/D −46°, c = 1 in methanol
mp
99-102 °C (lit.)
General description
The crystals of (S)-(-)-4-oxo-2-azetidinecarboxylic acid are orthorhombic and belongs to P212121 space group.
Application
Important building block for the synthesis of NMDA receptor antagonists, 3-alkyl-L-aspartic acids, and orally active β-lactam inhibitors.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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)
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
Hanessian, S. et al.
Synlett, 33-33 (1992)
Baldwin, J.E. et al.
Tetrahedron, 51, 11581-11581 (1995)
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