1,3-thiazol-5-ylmethyl N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate

• ChemBase ID: 160512
• Molecular Formular: C23H27N3O3S
• Molecular Mass: 425.54378
• Monoisotopic Mass: 425.17731274
• SMILES: c1sc(cn1)COC(=O)N[C@H](C[C@H](O)[C@@H](N)Cc1ccccc1)Cc1ccccc1
• Canonical SMILES: O=C(N[C@@H](Cc1ccccc1)C[C@@H]([C@H](Cc1ccccc1)N)O)OCc1cncs1
• InChI: InChI=1S/C23H27N3O3S/c24-21(12-18-9-5-2-6-10-18)22(27)13-19(11-17-7-3-1-4-8-17)26-23(28)29-15-20-14-25-16-30-20/h1-10,14,16,19,21-22,27H,11-13,15,24H2,(H,26,28)/t19-,21-,22-/m0/s1
• InChIKey: WJLNUWNCHAHJJF-BVSLBCMMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-thiazol-5-ylmethyl N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• IUPAC Traditional name: 1,3-thiazol-5-ylmethyl N-[(2S,4S,5S)-5-amino-4-hydroxy-1,6-diphenylhexan-2-yl]carbamate
• Synonyms: 2S,3S,5S-2-Amino-5-[N-[[(5-thiozolyl)methoxy]carbonyl]amino]-1,6-diphenyl-3-hydroxyhexane

Database IDs

• CAS Number: 144164-10-3
• PubChem SID: 162254647
• PubChem CID: 10812314

CALCULATED PROPERTIES

• Acid pKa: 14.222247
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.16640803
• LogD (pH = 7.4): 1.3657415
• Log P: 3.106828
• Molar Refractivity: 117.4446 cm^3
• Polarizability: 45.993073 Å^3
• Polar Surface Area: 97.47 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 66-69°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A630520

An intermediate in the synthesis of Ritonavir.

REFERENCES

• Kempf, D., et al.: J. Med. Chem., 41, 602 (1998)