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

• ChemBase ID: 163484
• Molecular Formular: C15H21NO5
• Molecular Mass: 295.33094
• Monoisotopic Mass: 295.14197278
• SMILES: c1c(ccc(c1)[C@H](CC(=O)OC)NC(=O)OC(C)(C)C)O
• Canonical SMILES: COC(=O)C[C@@H](c1ccc(cc1)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C15H21NO5/c1-15(2,3)21-14(19)16-12(9-13(18)20-4)10-5-7-11(17)8-6-10/h5-8,12,17H,9H2,1-4H3,(H,16,19)/t12-/m0/s1
• InChIKey: XZJDLGRKFKSJCD-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 474295-85-7
• PubChem SID: 162257619
• PubChem CID: 59132617

CALCULATED PROPERTIES

• Acid pKa: 9.48496
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.2081587
• LogD (pH = 7.4): 2.2046676
• Log P: 2.2082036
• Molar Refractivity: 76.6086 cm^3
• Polarizability: 30.213448 Å^3
• Polar Surface Area: 84.86 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - B693615

Used in the preparation of Alzheimer's disease acetylcholinesterase/serotonin transporter inhibitors.

REFERENCES

• Kogen, H. et al.; Org. Lett. 4, 3359 (2002)