Hydrazine hydrate (1:1) → HCID 178446045, compound

HRID 1279184Notes

Reaction equation

HRID 1279184 reaction equation
[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:7]([NH:9][C@H:10]([C:18](OCC)=[O:19])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:17])[NH2:16])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:33][NH2:34].O>CO>[NH:1]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:33][NH2:34])=[O:19])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:17])[NH2:16])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178472555HCID 178472555, compound

Product 1

HCID 178446045HCID 178446045, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Z-Leu-Arg-OEt was dissolved in 500 mL of methanol. NH2NH2.H2O 150 mL was added with ice cooling to the solution, then the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, 500 mL of water was added to the obtained residue, then the product was extracted 5 times with 1000 mL of n-butanol. The extract was washed 4 times with 500 mL of water, then concentrated under reduced pressure. The resulting residue was solidified by treatment with ether, then it was dried. Thus, 209.7 g of Z-Leu-Arg-NHNH2 (74.1% yield) was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 500 mL of water
  2. additionwas added to the obtained residue
  3. extractionthe product was extracted 5 times with 1000 mL of n-butanol
  4. washThe extract was washed 4 times with 500 mL of water
  5. concentrationconcentrated under reduced pressure
  6. customit was dried

Sources & evidence

ORD record
ord-e6ab8379edf84513b4f5bc286700bbc0
Source dataset
uspto-grants-2002_09
Patent number
US06448031B1

Reaction notes

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