HCID 86756932, compound → HCID 86756931, compound

HRID 1979230Notes

Reaction equation

HRID 1979230 reaction equation
C([O:8][NH:9][C:10]([C@H:12]([C@@H:22]([CH2:48][CH:49]([CH3:51])[CH3:50])[C:23]([NH:25][N:26]([C:32](=[O:47])[CH2:33][CH2:34][CH2:35][NH:36]C(OCC1C=CC=CC=1)=O)[CH2:27][C@@H:28]([CH3:31])[CH2:29][CH3:30])=[O:24])[CH2:13]/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:11])C1C=CC=CC=1>CO.[Pd]>[NH2:36][CH2:35][CH2:34][CH2:33][C:32]([N:26]([CH2:27][C@@H:28]([CH3:31])[CH2:29][CH3:30])[NH:25][C:23](=[O:24])[C@@H:22]([C@@H:12]([C:10](=[O:11])[NH:9][OH:8])[CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:48][CH:49]([CH3:50])[CH3:51])=[O:47]

Participants

4

Reactant 1

HCID 86756932HCID 86756932, compound

Product 1

HCID 86756931HCID 86756931, compoundYield 70.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.216 g of (E)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-2′-(4-benzyloxycarbonylaminobutyryl)-4-methyl-2′-(2(S)-methylbutyl)valerohydrazide in 5 ml of methanol was hydrogenated in the presence of 0.1 g of 10% palladium-on-carbon catalyst for 1 hour. The catalyst was removed by filtration and the methanol was evaporated. The residue was re-evaporated from diethyl ether and then triturated with a mixture of diethyl ether and hexane and there was obtained 0.104 g of 2′-(4-aminobutyryl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methyl-2′-(2(S)-methylbutyl)valerohydrazide in the form of a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe methanol was evaporated
  3. customThe residue was re-evaporated from diethyl ether
  4. customtriturated with a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-26bdf82b1f8741d497eb9226928fa08c
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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