HCID 86757194, compound → HCID 86757193, compound

HRID 1386569Notes

Reaction equation

HRID 1386569 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][S:5]([N:8]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:9][C:10](=[O:37])[C@@H:11]([C@@H:16]([C:26](=[O:36])[NH:27][O:28]CC1C=CC=CC=1)[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:7])=[O:6].[H][H]>CO.[Pd]>[NH2:1][CH2:2][CH2:3][CH2:4][S:5]([N:8]([CH2:38][CH:39]([CH3:41])[CH3:40])[NH:9][C:10](=[O:37])[C@@H:11]([C@@H:16]([C:26](=[O:36])[NH:27][OH:28])[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:12][CH:13]([CH3:14])[CH3:15])(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 86757194HCID 86757194, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86757193HCID 86757193, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.15 g of (E)-2′-(3-aminopropanesulphonyl)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in 5 ml of methanol was hydrogenated in the presence of 60 mg of 10% palladium-on-charcoal until uptake of hydrogen was complete. The catalyst was removed by filtration and the solvent was evaporated. The residue was triturated with diethyl ether and there was obtained 0.088 g of 2′-(3-aminopropanesulphonyl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a pale pink 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-37cdaea86e6d4acc81871010f3f4f4f9
Source dataset
uspto-grants-2001_07
Patent number
US06265446B1

Reaction notes

Loading…