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

• ChemBase ID: 68524
• Molecular Formular: C16H18Cl2N2O4S
• Molecular Mass: 405.29612
• Monoisotopic Mass: 404.03643343
• SMILES: N12C(=C(CS[C@@H]1[C@@H](C2=O)N)CCl)C(=O)OCc1ccc(cc1)OC.Cl
• Canonical SMILES: ClCC1=C(C(=O)OCc2ccc(cc2)OC)N2[C@H](SC1)[C@@H](C2=O)N.Cl
• InChI: InChI=1S/C16H17ClN2O4S.ClH/c1-22-11-4-2-9(3-5-11)7-23-16(21)13-10(6-17)8-24-15-12(18)14(20)19(13)15;/h2-5,12,15H,6-8,18H2,1H3;1H/t12-,15-;/m1./s1
• InChIKey: LYIIGHOYDRRHAJ-XRZFDKQNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-methoxyphenyl)methyl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride
• IUPAC Traditional name: (4-methoxyphenyl)methyl (6R,7R)-7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride
• Synonyms: 7-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester hydrochloride; (6R,7R)-7-Amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (4-Methoxyphenyl)methyl Ester Hydrochloride; 7-Amino-3 chloromethyl-3-cephem-4-carboxylic Acid p-Methoxybenzyl Ester Hydrochloride

Database IDs

• CAS Number: 113479-65-5
• MDL Number: MFCD00191255
• PubChem SID: 162034255
• PubChem CID: 14032024

CALCULATED PROPERTIES

• Acid pKa: 15.404817
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.54991376
• LogD (pH = 7.4): 1.0171213
• Log P: 1.3097008
• Molar Refractivity: 92.4828 cm^3
• Polarizability: 36.181755 Å^3
• Polar Surface Area: 81.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 128-130°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - A603445

Cefazolin intermediate as antibacterials.

REFERENCES

• Brown, R., et al.: J. Med. Chem., 33, 2114 (1990)
• Minnick, A., et al.: J. Antimicrob. Agents Chemother., 36, 840 (1990)
• Tsuji, K., et al.: Bioorg. Med. Chem., 4, 2135 (1990)
• Kinzel, O., et al.: J. Antibiot., 51, 499 (1990)