Hydrazine hydrate (1:1) → N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(4-thiazolyl)-DL-alanine hydrazide

HRID 255627Notes

Reaction equation

HRID 255627 reaction equation
C[O:2][C:3](=O)[CH:4]([CH2:31][C:32]1[N:33]=[CH:34][S:35][CH:36]=1)[NH:5][C:6](=[O:30])[C@H:7]([CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].O.[NH2:39][NH2:40]>CN(C)C=O>[CH2:12]([O:11][C:9]([NH:8][C@H:7]([C:6]([NH:5][CH:4]([C:3]([NH:39][NH2:40])=[O:2])[CH2:31][C:32]1[N:33]=[CH:34][S:35][CH:36]=1)=[O:30])[CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53931154N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(4-thiazolyl)-DL-alanine methyl ester

Product 1

HCID 86741832N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(4-thiazolyl)-DL-alanine hydrazideYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.10 g (4.06 mmole) of this ester were dissolved in 20 ml of dimethylformamide, and then 2.00 g (40.0 mmole) of hydrazine hydrate were added; the mixture was stirred overnight at room temperature. This reaction product was condensed by evaporation under reduced pressure, and then water was added to the residue. The precipitating crystals were collected by filtration, washed with hexane and diethyl ether and dried, to yield 1.90 g (90.5%) of the title compound.

Workup

  1. customcondensed
  2. customby evaporation under reduced pressure
  3. additionwater was added to the residue
  4. filtrationThe precipitating crystals were collected by filtration
  5. washwashed with hexane and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-4c0fabb8bcaa44e19bbfd92a2f7d66d4
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

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