diphenylmethyl (6R,7R)-3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 176503
• Molecular Formular: C29H25ClN2O4S
• Molecular Mass: 533.0378
• Monoisotopic Mass: 532.12235597
• SMILES: [C@@H]12N(C(=C(CS1)CCl)C(=O)OC(c1ccccc1)c1ccccc1)C(=O)[C@H]2NC(=O)Cc1ccccc1
• Canonical SMILES: ClCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1ccccc1
• InChI: InChI=1S/C29H25ClN2O4S/c30-17-22-18-37-28-24(31-23(33)16-19-10-4-1-5-11-19)27(34)32(28)25(22)29(35)36-26(20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,24,26,28H,16-18H2,(H,31,33)/t24-,28-/m1/s1
• InChIKey: BCMPVBNNIHFSLU-UFHPHHKVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenylmethyl (6R,7R)-3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: diphenylmethyl (6R,7R)-3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: 3-Cloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl Ester; 7-Phenylacetamide-3-chloromethyl-3-cephem-4-carboxylic Acid Diphenylmethyl Ester

Database IDs

• CAS Number: 64308-63-0
• PubChem SID: 164232413
• PubChem CID: 11145881

CALCULATED PROPERTIES

• Acid pKa: 11.501809
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.9047985
• LogD (pH = 7.4): 4.904768
• Log P: 4.9047985
• Molar Refractivity: 144.4681 cm^3
• Polarizability: 56.138844 Å^3
• Polar Surface Area: 75.71 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 124-126°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P319100

An intermediate in the synthesis of various beta-lactam antibiotics.

REFERENCES

• Jones, R., et al.: J. Clin. Microbiol.,15, 677 (1982)
• Matagne, A., et al.: Biochem. J., 330, 581 (1982)
• Zlokarnik, G., et al.: Science, 279, 84 (1982)