tert-butyl N-[(2R,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

• ChemBase ID: 161620
• Molecular Formular: C25H37N3O5S
• Molecular Mass: 491.64338
• Monoisotopic Mass: 491.2453923
• 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
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)N)C[C@H]([C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)O)C
• InChI: InChI=1S/C25H37N3O5S/c1-18(2)16-28(34(31,32)21-13-11-20(26)12-14-21)17-23(29)22(15-19-9-7-6-8-10-19)27-24(30)33-25(3,4)5/h6-14,18,22-23,29H,15-17,26H2,1-5H3,(H,27,30)/t22-,23-/m1/s1
• InChIKey: GSFKNEPGHWUCQO-DHIUTWEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2R,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2R,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
• Synonyms: [(1S,2R)-3-[[(4-Aminophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]carbamic Acid 1,1-Dimethylethyl Ester; [(1S,2R)-1-Benzyl-2-hydroxy-3-[isobutyl-[(4-aminophenyl)sulfonyl]amino]propyl]carbamic Acid tert-Butyl Ester

Database IDs

• CAS Number: 183004-94-6
• PubChem SID: 162255755
• PubChem CID: 71313846

CALCULATED PROPERTIES

• Acid pKa: 13.6967125
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.5793538
• LogD (pH = 7.4): 3.5796816
• Log P: 3.579686
• Molar Refractivity: 134.277 cm^3
• Polarizability: 52.80708 Å^3
• Polar Surface Area: 121.96 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - B279950

Darunavir intermediate, a potent inhibitor of HIV-1 protease.

REFERENCES

• Debouck, C., et al.: Drug Dev. Res., 21, 1 (1990)
• Krohn, A., et al.: J. Med. Chem., 34, 3340 (1990)
• Sham, H., et al.: Antimicrob. Agents Chemother., 42, 3218 (1990)