Hydrochloric Acid → HCID 26527813, compound

HRID 2393102Notes

Reaction equation

HRID 2393102 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].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([NH:6][S:25]([C:22]1[CH:23]=[CH:24][C:19]([Br:18])=[CH:20][CH:21]=1)(=[O:27])=[O:26])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7396p-Bromobenzenesulfonyl chlorideHCID 11448200methyl (2R)-2-amino-3-(1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 26527813HCID 26527813, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1 g (3.9 mmol) of D-tryptophan methyl ester hydrochloride in 12 mL of pyridine at ambient temperature is added 1 g (3.9 mmol) of 4-bromobenzene sulfonyl chloride. The yellow mixture is allowed to stir overnight. It is then poured into aqueous 10% HCl and extracted with several portions of ethyl acetate. The combined organic phases are washed with aqueous 10% HCl, water, and brine, and dried over sodium sulfate. The solution is decolorized with activated charcoal, and concentrated to 1.1 g (65%) of a white solid.

Workup

  1. extractionextracted with several portions of ethyl acetate
  2. washThe combined organic phases are washed with aqueous 10% HCl, water, and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to 1.1 g (65%) of a white solid

Sources & evidence

ORD record
ord-6c0e35e4df4644ee87bf7cd0894c5712
Source dataset
uspto-grants-1998_09
Patent number
US05804593

Reaction notes

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