Hydrochloric Acid → L-Tryptophan ethyl ester hydrochloride (1:1)

HRID 2082003Notes

Reaction equation

HRID 2082003 reaction equation
[NH2:1][C@H: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.[ClH:16].[CH2:17](O)[CH3:18]>>[ClH:16].[CH2:17]([O:14][C:13](=[O:15])[C@H: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])[CH3:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6305L-Tryptophan

Product 1

HCID 134519L-Tryptophan ethyl ester hydrochloride (1:1)

Procedure

A mixture of L-tryptophan (14.3 g, 0.07 mol) in 200 ml of ethanol containing ~7 g of anhydrous HCl was refluxed for 5 hours. The mixture was cooled and the solid which separated was recrystallized from ethanol/ether. Yield 17.4 g (92.5%), m.p. 226°-228° C. The product has the formula: ##STR1587## The product may also be named ethyl L-2-amino-3-indolepropionate.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureThe mixture was cooled
  3. customthe solid which separated
  4. customwas recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-86d16707902f4cd3bce67f3cc394296e
Source dataset
uspto-grants-1993_02
Patent number
US05187158

Reaction notes

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