benzyl N-[1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamate

• ChemBase ID: 163640
• Molecular Formular: C19H19N3O3
• Molecular Mass: 337.37246
• Monoisotopic Mass: 337.14264148
• SMILES: c1ccc2c(c1)c(c[nH]2)CC(NC(=O)OCc1ccccc1)C(=O)N
• Canonical SMILES: O=C(NC(C(=O)N)Cc1c[nH]c2c1cccc2)OCc1ccccc1
• InChI: InChI=1S/C19H19N3O3/c20-18(23)17(10-14-11-21-16-9-5-4-8-15(14)16)22-19(24)25-12-13-6-2-1-3-7-13/h1-9,11,17,21H,10,12H2,(H2,20,23)(H,22,24)
• InChIKey: GGRKLCWXRBTPLH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamate
• IUPAC Traditional name: benzyl N-[1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamate
• Synonyms: (1-Carbamoyl-2-indol-3-ylethyl)carbamic Acid Benzyl Ester; Carbobenzoxy-D,L-tryptophanamide

Database IDs

• CAS Number: 27018-75-3
• PubChem SID: 162257775
• PubChem CID: 582531

CALCULATED PROPERTIES

• Acid pKa: 13.61156
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 2.5320454
• LogD (pH = 7.4): 2.5320451
• Log P: 2.5320454
• Molar Refractivity: 93.705 cm^3
• Polarizability: 37.435017 Å^3
• Polar Surface Area: 97.21 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 166-168°C

DETAILS

Toronto Research Chemicals - C176000

An amino acid amide and intermediate in the preparation of L-Tryptophanamide Hydrochloride (Cat. #T89550).

REFERENCES

• Smith, E.L., and Polglase, W.J.: J. Biol. Chem., 180, 1209 (1949)