Hydrazine hydrate (1:1) → HCID 131713323, compound

HRID 905095Notes

Reaction equation

HRID 905095 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([OH:16])=O)=[O:11])=[O:7])([CH3:4])[CH3:3].[NH2:17][C@H:18]([C:26]([O:28]C)=O)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O.[NH2:31][NH2:32]>CO>[NH:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]([NH:12][CH2:13][C:14]([NH:17][C@H:18]([C:26]([NH:31][NH2:32])=[O:28])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])=[O:11]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131713324HCID 131713324, compound

Product 1

HCID 131713323HCID 131713323, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Boc-Gly-GLy-Phe-OMe (8.0 g., 20 mM) was dissolved in methanol (25 ml.), and 95% v/v hydrazine hydrate (3.2 ml.) was added. The mixture was kept at room temperature for 24 hours and then evaporated. The residue was chromatographed on a column of silica gel equibrated and eluted with methanol/chloroform 1:9 v/v. The fractions which contained the required hydrazide were combined and evaporated to give Boc-Gly-Gly-Phe-NHNH2, RfP 0.6, RfQ 0.3.

Workup

  1. customevaporated
  2. customThe residue was chromatographed on a column of silica gel
  3. washeluted with methanol/chloroform 1:9 v/v
  4. customevaporated

Sources & evidence

ORD record
ord-72a242acd18e447c9ff4a81a0d3142cd
Source dataset
uspto-grants-1983_12
Patent number
US04421744

Reaction notes

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