HCID 86756905, compound → HCID 86756904, compound

HRID 1979212Notes

Reaction equation

HRID 1979212 reaction equation
C(OC([NH:11][C@@H:12]([C:14]([N:16]([CH2:46][CH:47]([CH3:49])[CH3:48])[NH:17][C:18](=[O:45])[C@@H:19]([CH:24]([C:34](=[O:44])[NH:35][O:36]CC1C=CC=CC=1)[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:15])[CH3:13])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@@H:12]([C:14]([N:16]([CH2:46][CH:47]([CH3:49])[CH3:48])[NH:17][C:18](=[O:45])[C@@H:19]([CH:24]([C:34](=[O:44])[NH:35][OH:36])[CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:15])[CH3:13]

Participants

4

Reactant 1

HCID 86756905HCID 86756905, compound

Product 1

HCID 86756904HCID 86756904, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.820 g of 2′-(N-benzyloxycarbonyl-D-alanyl)-2(R)-[1(RS)-[(benzyloxy)carbamoyl]-4-phenylbutyl]-2′-isobutyl-4-methylvalerohydrazide in 20 ml methanol was hydrogenated in the presence of 0.240 g of 5% palladium-on-carbon for 1.5 hours. The catalyst was removed by filtration and the solvent was evaporated. The residue was triturated with diethyl ether to give 0.480 g of 2′-(D-alanyl)-2(R)-[1(RS)-(hydroxycarbamoyl)-4-phenylbutyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a colorless glass.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-d898e15d55424aaf82d3c20b774f9158
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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