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

• ChemBase ID: 159961
• Molecular Formular: C21H20Cl2N2O3S
• Molecular Mass: 451.3661
• Monoisotopic Mass: 450.05716887
• SMILES: [C@@H]12N(C(=C(CS1)CCl)C(=O)OC(c1ccccc1)c1ccccc1)C(=O)[C@H]2N.Cl
• Canonical SMILES: ClCC1=C(C(=O)OC(c2ccccc2)c2ccccc2)N2[C@H](SC1)[C@@H](C2=O)N.Cl
• InChI: InChI=1S/C21H19ClN2O3S.ClH/c22-11-15-12-28-20-16(23)19(25)24(20)17(15)21(26)27-18(13-7-3-1-4-8-13)14-9-5-2-6-10-14;/h1-10,16,18,20H,11-12,23H2;1H/t16-,20-;/m1./s1
• InChIKey: HDYOATPRFNMLSX-KYSFMIDTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenylmethyl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride
• IUPAC Traditional name: diphenylmethyl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride
• Synonyms: (6R,7R)-7-Amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl Ester Hydrochloride; (6R-trans)-7-Amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl Ester Monohydrochloride; 7-Amino-3-chloromethyl-3-cephem-4-carboxylic Acid Diphenylmethyl Ester Hydrochloride

Database IDs

• CAS Number: 79349-53-4
• PubChem SID: 162254096
• PubChem CID: 13239628

CALCULATED PROPERTIES

• Acid pKa: 15.404687
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3919977
• LogD (pH = 7.4): 2.9590328
• Log P: 3.2516122
• Molar Refractivity: 110.3024 cm^3
• Polarizability: 43.184486 Å^3
• Polar Surface Area: 72.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A603615

An important intermediate in the preparation of cephalosporin antibiotics.

REFERENCES

• Yamanaka, H. et al.: J. Antibiot., 38, 1738 (1738)
• Nakayama, E. et al.: J. Antibiot., 44, 854 (1738)