Hydrazine hydrate (1:1) → N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(2-thienyl)-DL-alanine hydrazide

HRID 255624Notes

Reaction equation

HRID 255624 reaction equation
CO[C:3](=[O:37])[CH:4]([CH2:31][C:32]1[S:33][CH:34]=[CH: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]C1C=CC=CC=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:37])[CH2:31][C:32]1[S:33][CH:34]=[CH: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:20]1[CH:29]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13961462N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(2-thienyl)-DL-alanine methyl ester

Product 1

HCID 13961464N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(2-thienyl)-DL-alanine hydrazideYield 967.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixed solution of 1.0 g (194 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(2-thienyl)-DL-alanine methyl ester and 0.64 g (0.2 mmole) of 80% hydrazine hydrate in 10 ml of dimethylformamide was stirred for 2 hours at room temperature and then left standing overnight at room temperature. Dimethylformamide was removed by evaporation under reduced pressure. Water was added to the residue, and the mixture was stirred to form a powdery precipitate, which was collected by filtration, washed with a mixture of diethyl ether and hexane and dried to yield 1.0 g (100%) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(2-thienyl)-DL-alanine hydrazide melting at 163°-164° C.

Workup

  1. waitleft
  2. customDimethylformamide was removed by evaporation under reduced pressure
  3. additionWater was added to the residue
  4. customto form a powdery precipitate, which
  5. filtrationwas collected by filtration
  6. washwashed with a mixture of diethyl ether and hexane
  7. customdried

Sources & evidence

ORD record
ord-ca4b8e9e72b84ba2b55b510a852d662a
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

Loading…