tert-butyl N-[(2S,3R)-3-hydroxy-4-{N-[2-(2H3)methyl(2H6)propyl]4-nitrobenzenesulfonamido}-1-phenylbutan-2-yl]carbamate

• ChemBase ID: 161570
• Molecular Formular: C25H35N3O7S
• Molecular Mass: 521.6263
• Monoisotopic Mass: 521.21957148
• SMILES: c1c(ccc(c1)S(=O)(=O)N(C[C@H]([C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)O)CC(C)C)[N+](=O)[O-]
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)[N+](=O)[O-])C[C@H]([C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)O)C
• InChI: InChI=1S/C25H35N3O7S/c1-18(2)16-27(36(33,34)21-13-11-20(12-14-21)28(31)32)17-23(29)22(15-19-9-7-6-8-10-19)26-24(30)35-25(3,4)5/h6-14,18,22-23,29H,15-17H2,1-5H3,(H,26,30)/t22-,23+/m0/s1
• InChIKey: CQGKCZKCWMWXQP-XZOQPEGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S,3R)-3-hydroxy-4-{N-[2-(^2H₃)methyl(^2H₆)propyl]4-nitrobenzenesulfonamido}-1-phenylbutan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S,3R)-3-hydroxy-4-{N-[2-(^2H₃)methyl(^2H₆)propyl]4-nitrobenzenesulfonamido}-1-phenylbutan-2-yl]carbamate
• Synonyms: N-[(1S,2R)-2-Hydroxy-3-[(2-methylpropyl-d9)[(4-nitrophenyl)sulfonyl]amino]-1-(phenylmethyl)propyl]carbamic Acid 1,1-Dimethylethyl Ester; [(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-d9-[(4-nitrophenyl)sulfonyl]amino]propyl]carbamic Acid tert-Butyl Ester

Database IDs

• PubChem SID: 162255705
• PubChem CID: 46780735

CALCULATED PROPERTIES

• Acid pKa: 13.46877
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 4.348596
• LogD (pH = 7.4): 4.3485956
• Log P: 4.348596
• Molar Refractivity: 136.9013 cm^3
• Polarizability: 53.576313 Å^3
• Polar Surface Area: 141.76 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B279072

An intermediate in the synthesis of labelled Amprenavir, a selective HIV protease inhibitor.

REFERENCES

• Dorsey, B., et al.: J. Med. Chem., 37, 3443 (1994)
• Gong, Y., et al.: Antimicrob. Agents Chemother., 44, 2319 (1994)
• Maeda, K., et al.: J. Biol. Chem., 276, 35194 (1994)