tert-butyl 2-{[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino]oxy}-2-methylpropanoate

• ChemBase ID: 70531
• Molecular Formular: C20H22N4O4S3
• Molecular Mass: 478.60808
• Monoisotopic Mass: 478.0803182
• SMILES: C(=O)(C(C)(C)O/N=C(\C(=O)Sc1sc2c(n1)cccc2)/c1nc(sc1)N)OC(C)(C)C
• Canonical SMILES: Nc1scc(n1)/C(=N/OC(C(=O)OC(C)(C)C)(C)C)/C(=O)Sc1nc2c(s1)cccc2
• InChI: InChI=1S/C20H22N4O4S3/c1-19(2,3)27-16(26)20(4,5)28-24-14(12-10-29-17(21)22-12)15(25)31-18-23-11-8-6-7-9-13(11)30-18/h6-10H,1-5H3,(H2,21,22)/b24-14-
• InChIKey: RCZJVHXVCSKDKB-OYKKKHCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl 2-{[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino]oxy}-2-methylpropanoate
• IUPAC Traditional name: tert-butyl 2-{[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-(1,3-benzothiazol-2-ylsulfanyl)-2-oxoethylidene]amino]oxy}-2-methylpropanoate
• Synonyms: (Z)-tert-Butyl 2-(((1-(2-aminothiazol-4-yl)-2-(benzo[d]thiazol-2-ylthio)-2-oxoethylidene)amino)oxy)-2-methylpropanoate; 2-[[(Z)-[1-(2-Amino-4-thiazolyl)-2-(2-benzothiazolylthio)-2-oxoethylidene]amino]oxy]-2-methylpropanoic Acid 1,1-Dimethylethyl Ester; 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl)isopropoxyiminoacetate

Database IDs

• CAS Number: 89604-92-2
• PubChem SID: 162036246
• PubChem CID: 13577862

CALCULATED PROPERTIES

• Acid pKa: 16.336672
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 5.7875366
• LogD (pH = 7.4): 5.793403
• Log P: 5.7934785
• Molar Refractivity: 120.9703 cm^3
• Polarizability: 47.96302 Å^3
• Polar Surface Area: 116.76 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Warm Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 184-187°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 - M252610

An intermediate for the preparation of cephalosporin derivatives.

REFERENCES

• Albrecht, H. A., et al.: J. Med. Chem., 37, 400 (1994)