Triethylamine → L-Tryptophan, methyl ester

HRID 615256Notes

Reaction equation

HRID 615256 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 77980L-Tryptophan, methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The tryptophan methylester hydrochloride thus obtained was suspended in 1 liter of ethyl acetate and 100 ml of triethylamine was added thereto. The mixture was allowed to react for 1 hour while vigorously stirring. The insoluble matter (i.e. triethylamine hydrochloride) was filtered off and the filtrate was washed with a small amount of water. Thereafter, the solvent was distilled off to obtain 40 g of oily tryptophan methylester.

Workup

  1. customto react for 1 hour
  2. filtrationThe insoluble matter (i.e. triethylamine hydrochloride) was filtered off
  3. washthe filtrate was washed with a small amount of water
  4. distillationThereafter, the solvent was distilled off

Sources & evidence

ORD record
ord-02c597c28c3941fba757be411839b279
Source dataset
uspto-grants-1985_02
Patent number
US04497957

Reaction notes

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