Hydrazine → BOC-Lys(CBZ)-Gln-Nle-NHNH2

HRID 649092Notes

Reaction equation

HRID 649092 reaction equation
[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:2]([C:18]([NH:20][C@H:21]([C:27]([NH:29][C@H:30]([C:35](OC)=[O:36])[CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH2:22][CH2:23][C:24](=[O:26])[NH2:25])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[NH2:46][NH2:47]>CN(C=O)C>[NH:1]([C:39]([O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:40])[C@H:2]([C:18]([NH:20][C@H:21]([C:27]([NH:29][C@H:30]([C:35]([NH:46][NH2:47])=[O:36])[CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH2:22][CH2:23][C:24](=[O:26])[NH2:25])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 131715496BOC-Lys(CBZ)-Gln-Nle-OMe

Product 1

HCID 131715497BOC-Lys(CBZ)-Gln-Nle-NHNH2Yield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The tripeptide methyl ester (XIII) (1 g, 1.6 mmol) was suspended in DMF (5 ml), hydrazine (0.8 g, 0.78 ml, 16 mmol) was added and the mixture was stirred overnight. The solvent was removed in vacuo and the residue solidified using MeOH/EtOAc to give (XIV) (0.9 g, 90%). T.l.c. RfA3 =0.70 This was used immediately in the next step.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-323cb86147c247598df9a1e9c405bad0
Source dataset
uspto-grants-1988_04
Patent number
US04737487

Reaction notes

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