HCID 86756908, compound → HCID 86756907, compound

HRID 1979215Notes

Reaction equation

HRID 1979215 reaction equation
C(OC([NH:11][C@@H:12]([C:14]([N:16]([CH2:40][CH:41]([CH3:43])[CH3:42])[NH:17][C:18](=[O:39])[C@@H:19]([CH:24]([C:28](=[O:38])[NH:29][O:30]CC1C=CC=CC=1)[CH2:25][CH:26]=[CH2:27])[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]([CH2:40][CH:41]([CH3:42])[CH3:43])[NH:17][C:18](=[O:39])[C@@H:19]([CH:24]([C:28](=[O:38])[NH:29][OH:30])[CH2:25][CH2:26][CH3:27])[CH2:20][CH:21]([CH3:23])[CH3:22])=[O:15])[CH3:13]

Participants

4

Reactant 1

HCID 86756908HCID 86756908, compound

Product 1

HCID 86756907HCID 86756907, compoundYield 136.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.560 g of 2′-(N-benzyloxycarbonyl-D-alanyl)-2(R)-[1(RS)-[(benzyloxy)carbamoyl]-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 25 ml of methanol was hydrogenated in the presence of 0.150 g of 5% palladium-on-carbon for 2 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)butyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid. This solid was then dissolved in 2 ml of dioxan and the solution was treated with 0.5 ml of 4M hydrogen chloride in dioxan. The mixture was stirred at room temperature for 15 minutes and then diluted with diethyl ether. Filtration and drying gave 0.188 g of 2′-(D-alanyl)-2(R)-[1(RS)-(hydroxycarbamoyl)butyl]-2′-isobutyl-4-methylvalerohydrazide hydrochloride in the form of a white solid.

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-e6daf2008a5941bc9225719eefb967ab
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

Loading…