Ammonium Hydroxide → (S)-5-Hydroxytryptophan amide

Reaction equation

Cl.CO[C:4](=[O:18])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[NH:10][CH:9]=1)[NH2:6].[OH-].[NH4+:20]>>[OH:17][C:14]1[CH:15]=[C:16]2[C:11]([NH:10][CH:9]=[C:8]2[CH2:7][C@@H:5]([C:4]([NH2:20])=[O:18])[NH2:6])=[CH:12][CH:13]=1

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 24802218methyl (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 9899303(S)-5-Hydroxytryptophan amide

Procedure

(S)-5-Hydroxytryptophan methyl ester hydrochloride (0.247 g, 0.91 mmol) was stirred overnight at room temperature in ammonium hydroxide (10 mL). After removal of volatiles under vacuum, the title compound of example 44 was obtained as a dark solid.

Workup

customAfter removal of volatiles under vacuum

Sources & evidence

ORD record: ord-a6638a3dc1e34de09f15bc33e5dd0439
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479508B1

Reaction notes

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