Hydrazine hydrate (1:1) → HCID 86756920, compound

HRID 1979223Notes

Reaction equation

HRID 1979223 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:46][CH:47]([CH3:49])[CH3:48])[C:22]([NH:24][N:25]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:26][C@H:27]([N:29]1C(=O)C2=CC=CC=C2C1=O)[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/C1C=CC=CC=1)=[O:10].[OH2:50].NN>CO>[NH2:29][C@@H:27]([C:26]([N:25]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[NH:24][C:22](=[O:23])[C@@H:21]([C@@H:11]([C:9](=[O:10])[NH:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:12]/[CH:13]=[CH:14]/[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:50])[CH3:28]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86756921HCID 86756921, compound

Product 1

HCID 86756920HCID 86756920, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.22 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methyl-2′-phenyl-2′-(2(R)-phthalimidopropyl)valerohydrazide in 4 ml of methanol was treated with 0.04 g of hydrazine hydrate. The mixture was stirred for 5.5 hours and then the solvent was evaporated. The residue was suspended in 2 ml of dichloromethane and stirred at 4° C. overnight. The suspended solid was filtered off, the filtrate was evaporated and the residue was purified by flash chromatography on silica gel using dichloromethane/methanol (20:1) for the elution. There was obtained 0.189 of (E)-2′-(D-alanyl)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methyl-2′-phenylvalerohydrazide in the form of a colorless foam.

Workup

  1. customthe solvent was evaporated
  2. stirringstirred at 4° C. overnight
  3. filtrationThe suspended solid was filtered off
  4. customthe filtrate was evaporated
  5. customthe residue was purified by flash chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-b28ee18479504ed1b5bbc2819dee62cd
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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