Methanol → methyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

HRID 615255

Reaction equation

HRID 615255 reaction equation
[NH2:1][CH:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.S(Cl)([Cl:18])=O.[CH3:20]O>>[ClH:18].[CH3:20][O:14][C:13](=[O:15])[CH:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1148Dl-TryptophanHCID 24386Thionyl Chloride

Product 1

HCID 2827264methyl 2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Procedure

50 g of DL-tryptophan available from Nakarai Chemicals, Kyoto, Japan, was suspended in 500 ml of methanol and 40 ml of thionyl chloride was dropwise added thereto while vigorously stirring. The reaction was exothermic and the reaction mixture was allowed to be refluxed for 10 hours while stirring. Then, the solvent was distilled off and the resultant residue was washed with diethylether. Thus, DL-tryptophan methylester hydrochloride was obtained in the form of white crystals.

Workup

  1. temperatureto be refluxed for 10 hours
  2. stirringwhile stirring
  3. distillationThen, the solvent was distilled off
  4. washthe resultant residue was washed with diethylether

Sources & evidence

ORD record
ord-470d02e5100e4955bcb4e8f5514d2070
Source dataset
uspto-grants-1985_02
Patent number
US04497957

Linked notes

Loading…