Hydrazine hydrate (1:1) → HCID 178453392, compound

HRID 1580884Notes

Reaction equation

HRID 1580884 reaction equation
[NH:1]([C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])[C@H:2]([C:7]([NH:9][C@H:10]([C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:44]([O:46]C)=O)[CH2:38][C:39]1[N:43]=[CH:42][NH:41][CH:40]=1)=[O:35])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].O.[NH2:59][NH2:60]>CN(C)C=O.CO>[NH:1]([C:48]([O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:49])[C@H:2]([C:7]([NH:9][C@H:10]([C:23]([NH:25][C@H:26]([C:34]([NH:36][C@H:37]([C:44]([NH:59][NH2:60])=[O:46])[CH2:38][C:39]1[N:43]=[CH:42][NH:41][CH:40]=1)=[O:35])[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:24])[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178501420HCID 178501420, compound

Product 1

HCID 178453392HCID 178453392, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

3.97 g of Z-Asn-Lys(BOC)-Phe-His-OMe are dissolved in 8 ml of warm dimethylformamide and 12 ml of methanol. 2.5 ml of hydrazine hydrate are added to the solution whilst it is still at about 30°C and the mixture is allowed to stand for 20 hours at room temperature. The peptide-hydrazide is precipitated by adding water, filtered off and washed with water until free of hydrazine. The product is recrystallised from ethanol, melting point = 200°-201°C. In a thin layer chromatogram on silica gel RF43C = 0.5.

Workup

  1. customis still at about 30°C
  2. customThe peptide-hydrazide is precipitated
  3. additionby adding water
  4. filtrationfiltered off
  5. washwashed with water until free of hydrazine
  6. customThe product is recrystallised from ethanol, melting point = 200°-201°C

Sources & evidence

ORD record
ord-c1d802267f57413cb69fe5581fc0d755
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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