methyl (3S)-3-[4-(benzyloxy)phenyl]-3-{[(tert-butoxy)carbonyl]amino}propanoate

• ChemBase ID: 163483
• Molecular Formular: C22H27NO5
• Molecular Mass: 385.45348
• Monoisotopic Mass: 385.18892297
• SMILES: c1c(ccc(c1)[C@H](CC(=O)OC)NC(=O)OC(C)(C)C)OCc1ccccc1
• Canonical SMILES: COC(=O)C[C@@H](c1ccc(cc1)OCc1ccccc1)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C22H27NO5/c1-22(2,3)28-21(25)23-19(14-20(24)26-4)17-10-12-18(13-11-17)27-15-16-8-6-5-7-9-16/h5-13,19H,14-15H2,1-4H3,(H,23,25)/t19-/m0/s1
• InChIKey: HWUHPKYXIBZDMX-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[4-(benzyloxy)phenyl]-3-{[(tert-butoxy)carbonyl]amino}propanoate
• IUPAC Traditional name: methyl (3S)-3-[4-(benzyloxy)phenyl]-3-[(tert-butoxycarbonyl)amino]propanoate
• Synonyms: (βS)-β-[[(1,1-Dimethylethoxy)carbonyl]amino]-4-phenylmethoxy-benzenepropanoic Acid Methyl Ester; (βS)-β-[(1,1-tert-Butyloxycarbonyl)amino]-4-benzyloxy-benzenepropanoic Acid Methyl Ester

Database IDs

• PubChem SID: 162257618
• PubChem CID: 11429084

CALCULATED PROPERTIES

• Acid pKa: 13.82264
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.078571
• LogD (pH = 7.4): 4.0785704
• Log P: 4.078571
• Molar Refractivity: 105.7035 cm^3
• Polarizability: 41.67476 Å^3
• Polar Surface Area: 73.86 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B693610

Used in the preparation of Maraviroc (M193000) and its derivatives.