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-e1014672ce81403e92305650bdc5495f
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06794404B2

Reaction notes

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