(6R,7R)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 159915
• Molecular Formular: C7H7ClN2O3S
• Molecular Mass: 234.66008
• Monoisotopic Mass: 233.98659077
• SMILES: C1(=O)[C@H]([C@@H]2N1C(=C(CS2)Cl)C(=O)O)N
• Canonical SMILES: O=C1[C@@H](N)[C@@H]2N1C(=C(CS2)Cl)C(=O)O
• InChI: InChI=1S/C7H7ClN2O3S/c8-2-1-14-6-3(9)5(11)10(6)4(2)7(12)13/h3,6H,1,9H2,(H,12,13)/t3-,6-/m1/s1
• InChIKey: OQSAFIZCBAZPMY-AWFVSMACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R,7R)-7-Amino-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 3-Chloro-7-amino-3-cephem-4-carboxylic Acid; (6R-trans)-7-amino-3-chloro-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-Amino-3-chlorocephalosporanic Acid; 7-Amino-3-chloro-3-cephem-4-carboxylic acid

Database IDs

• CAS Number: 53994-69-7
• PubChem SID: 162254050
• PubChem CID: 6998927

CALCULATED PROPERTIES

• Acid pKa: 2.9637938
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.1385946
• LogD (pH = 7.4): -3.4176698
• Log P: -3.1372151
• Molar Refractivity: 52.4004 cm^3
• Polarizability: 20.295874 Å^3
• Polar Surface Area: 83.63 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid
• Apperance: Pale Yellow Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A603305

7-Amino-3-chloro-3-cephem-4-carboxylic acid is used as an intermediate in the preparation of semi-synthetic cephalosprin antibiotics.

REFERENCES

• Yang, L. et al.: Biotechnol. Lett., 25, 1195 (2003)
• Zhang, Y. et al.: Biocatal. Biotransform., 25, 59 (2003)