methyl (2S)-3-(1H-indol-3-yl)-2-[(methoxycarbonyl)amino]propanoate

• ChemBase ID: 145929
• Molecular Formular: C14H16N2O4
• Molecular Mass: 276.28784
• Monoisotopic Mass: 276.111007
• SMILES: COC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)OC
• Canonical SMILES: COC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)OC
• InChI: InChI=1S/C14H16N2O4/c1-19-13(17)12(16-14(18)20-2)7-9-8-15-11-6-4-3-5-10(9)11/h3-6,8,12,15H,7H2,1-2H3,(H,16,18)/t12-/m0/s1
• InChIKey: IYEKFSMKXYQRLC-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-3-(1H-indol-3-yl)-2-[(methoxycarbonyl)amino]propanoate
• IUPAC Traditional name: methyl (2S)-3-(1H-indol-3-yl)-2-[(methoxycarbonyl)amino]propanoate
• Synonyms: Nα-Methoxycarbonyl-L-tryptophan methyl ester; N-(Methoxycarbonyl)-L-tryptophan Methyl Ester; Nα-Methoxycarbonyl L-Tryptophan Methyl Ester; Nα-甲氧羰基-L-色氨酸甲酯

Database IDs

• CAS Number: 58635-46-4
• MDL Number: MFCD00075486
• PubChem SID: 24862389; 162240129
• PubChem CID: 7018187

CALCULATED PROPERTIES

• Acid pKa: 13.431923
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.7604089
• LogD (pH = 7.4): 1.7604085
• Log P: 1.7604089
• Molar Refractivity: 72.0393 cm^3
• Polarizability: 29.246653 Å^3
• Polar Surface Area: 80.42 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 99-101 °C(lit.); 99-101°C
• Optical Rotation: [α]20/D -1.4°, c = 1 in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C14H16N2O4

DETAILS

Sigma Aldrich - 367060

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - M261700

Nα-Methoxycarbonyl L-Tryptophan is used in the synthesis of (-)-Calycanthine, (+)-Chimonanthine, and (+)-Folicanthine.

REFERENCES

• Taniguchi, M., et al.: Chem. Pharm. Bull., 1983, 31, 1856 (1983)
• Verotta, L., et al.: Bioorg. Med. Chem., 10, 2133 (1983)