methyl (2S)-3-(3-acetyl-4-hydroxyphenyl)-2-{[(benzyloxy)carbonyl]amino}propanoate

• ChemBase ID: 159173
• Molecular Formular: C20H21NO6
• Molecular Mass: 371.38384
• Monoisotopic Mass: 371.1368874
• SMILES: c1c(c(ccc1C[C@H](NC(=O)OCc1ccccc1)C(=O)OC)O)C(=O)C
• Canonical SMILES: COC(=O)[C@H](Cc1ccc(c(c1)C(=O)C)O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C20H21NO6/c1-13(22)16-10-15(8-9-18(16)23)11-17(19(24)26-2)21-20(25)27-12-14-6-4-3-5-7-14/h3-10,17,23H,11-12H2,1-2H3,(H,21,25)/t17-/m0/s1
• InChIKey: MMFVAAWJEMBBJF-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-(3-acetyl-4-hydroxyphenyl)-2-{[(benzyloxy)carbonyl]amino}propanoate
• IUPAC Traditional name: methyl (2S)-3-(3-acetyl-4-hydroxyphenyl)-2-{[(benzyloxy)carbonyl]amino}propanoate
• Synonyms: 3-Acetyl-N-[(phenylmethoxy)carbonyl]-L-tyrosine Methyl Ester; 3-Acetyl-N-benzyloxycarbonyl-L-tyrosine Methyl Ester

Database IDs

• CAS Number: 110774-03-3
• PubChem SID: 162253308
• PubChem CID: 11810800

CALCULATED PROPERTIES

• Acid pKa: 10.115109
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.2901917
• LogD (pH = 7.4): 3.2893722
• Log P: 3.2902021
• Molar Refractivity: 97.9491 cm^3
• Polarizability: 38.01004 Å^3
• Polar Surface Area: 101.93 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - A171010

Protected L-DOPA (D533751) derivative.

REFERENCES

• Boger, D. & Yohannes, D.; J. Org. Chem. 52, 5283 (1987)