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

• ChemBase ID: 67691
• Molecular Formular: C24H23ClN2O5S
• Molecular Mass: 486.96782
• Monoisotopic Mass: 486.10162053
• SMILES: N12C(=C(CS[C@@H]1[C@@H](C2=O)NC(=O)Cc1ccccc1)CCl)C(=O)OCc1ccc(cc1)OC
• Canonical SMILES: ClCC1=C(C(=O)OCc2ccc(cc2)OC)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1ccccc1
• InChI: InChI=1S/C24H23ClN2O5S/c1-31-18-9-7-16(8-10-18)13-32-24(30)21-17(12-25)14-33-23-20(22(29)27(21)23)26-19(28)11-15-5-3-2-4-6-15/h2-10,20,23H,11-14H2,1H3,(H,26,28)/t20-,23-/m1/s1
• InChIKey: KFCMZNUGNLCSJQ-NFBKMPQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: (4-methoxyphenyl)methyl (6R,7R)-3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: 4-Methoxybenzyl 3-chloromethyl-7-(2-phenyl-acetamido)-3-cephem-4-carboxylate; (6R,7R)-3-(Chloromethyl)-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (4-Methoxyphenyl)methyl Ester; (6R-trans)-7-Phenylacetamido-3-(chloromethyl)-3-cephem-4-carboxylic Acid p-Methoxybenzyl Ester; GCLE; 4-Methoxybenzyl 3-Chloromethyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate

Database IDs

• CAS Number: 104146-10-3
• PubChem SID: 162033426
• PubChem CID: 10874591

CALCULATED PROPERTIES

• Acid pKa: 11.452807
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.9628868
• LogD (pH = 7.4): 2.962853
• Log P: 2.9628873
• Molar Refractivity: 126.6485 cm^3
• Polarizability: 49.116013 Å^3
• Polar Surface Area: 84.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 153-155°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - M226085

A key intermediate of cephem compounds.

REFERENCES

• Chambers, H., et al.: Antimicrob. Agents Chemother., 39, 2620 (1995)
• Heinisch, L., et al.: J. Med. Chem., 45, 3032 (1995)