Hydrazide (H3N21-) → (S)-5-Nitrotryptophan amide hydrochloride

HRID 1007701Notes

Reaction equation

HRID 1007701 reaction equation
[ClH:1].CO[C:4](=[O:20])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[NH:10][CH:9]=1)[NH2:6].[NH2:21][NH-]>O1CCOCC1>[ClH:1].[N+: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]([NH2:21])=[O:20])[NH2:6])=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 168365Hydrazide (H3N21-)HCID 86585256(S)-5-Nitrotryptophan methyl ester hydrochloride

Product 1

HCID 86585255(S)-5-Nitrotryptophan amide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-5-Nitrotryptophan methyl ester hydrochloride (see example 47) was converted to the corresponding amide derivative following the procedure described in example 44 for the 5-hydroxy derivative. The amino amide was then converted to its hydrochloride salt using 4N HCl in dioxane.

Sources & evidence

ORD record
ord-a7d084ad851b4da48f43ca66d712a601
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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