Hydrochloric Acid → 2-Amino-3-(2-oxoindolin-3-yl)propanoic acid hydrochloride

HRID 2309232Notes

Reaction equation

HRID 2309232 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].CS(C)=[O:19]>>[ClH:16].[NH2:1][CH:2]([CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:19])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 6305L-Tryptophan

Product 1

HCID 133932472-Amino-3-(2-oxoindolin-3-yl)propanoic acid hydrochloride

Procedure

10.2 Grams of L-tryptophane was suspended in 7.8 g of dimethyl sulfoxide, then 16.6 ml of concentrated hydrochloric acid was added all at once in the suspension, and the mixture was stirred at a room temperature overnight. The crystals formed in the reaction mixture were collected by filtration, then washed with acetone and dried to obtain 9.8 g of 2-amino-3-(oxindol-3-yl)propionic acid hydrochloride. [α]D20 +22.5° (C=1, methanol)

Workup

  1. customThe crystals formed in the reaction mixture
  2. filtrationwere collected by filtration
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-f618cb1792b546acbe72defd8242d106
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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