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

HRID 1746494Notes

Reaction equation

HRID 1746494 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][N:6]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]([CH2:9][C@@H:10]([C:12]([O-:14])=[O:13])[NH2:11])=[CH:7]1.[CH3:21]O>>[ClH:3].[CH3:5][N:6]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]([CH2:9][C@@H:10]([C:12]([O:14][CH3:21])=[O:13])[NH2:11])=[CH:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 866554521-methyl-L-tryptophanate

Product 1

HCID 67130420methyl (2S)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoate hydrochlorideYield 87%

Procedure

Thionyl chloride (16.7 mL) was added dropwise to methanol (150 mL) at 0° C., and thereafter 1-methyl-L-tryptophanate (10.0 g) was added at room temperature. The mixture was allowed to stir for 20 hours, and thereafter heated and refluxed for 6 hours. To the residue obtained by distilling off the solvent under a reduced pressure was added diethylether, and crystals precipitated were filtered, to give the captioned compound (10.7 g, 87%).

Workup

  1. temperatureheated
  2. temperaturerefluxed for 6 hours
  3. customTo the residue obtained
  4. distillationby distilling off the solvent under a reduced pressure
  5. additionwas added diethylether, and crystals
  6. customprecipitated
  7. filtrationwere filtered

Sources & evidence

ORD record
ord-7d756b5b76cd4f02bf3b35ec28d6ed9c
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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