HCID 88209454, compound → HCID 88210508, compound

HRID 651832Notes

Reaction equation

HRID 651832 reaction equation
[O:1]=[C:2]1[CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[C:4](=[O:11])[N:3]1[NH:12][C:13](=[O:40])[C@@H:14]([C@@H:19]([C:29](=[O:39])[NH:30][O:31]CC1C=CC=CC=1)[CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][CH:16]([CH3:18])[CH3:17]>CO.[Pd]>[O:1]=[C:2]1[CH:6]2[CH2:7][NH:8][CH2:9][CH2:10][N:5]2[C:4](=[O:11])[N:3]1[NH:12][C:13](=[O:40])[C@@H:14]([C@@H:19]([C:29](=[O:39])[NH:30][OH:31])[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 1

HCID 88209454HCID 88209454, compound

Product 1

HCID 88210508HCID 88210508, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.160 g of (E)-N-(1,2,3,5,6,7,8,8a(RS)-octahydro-1,3-dioxoimidazo[1,5-a]pyrazin-2-yl)-2(R)-[1(S)-(benzyloxycarbamoyl)-4-phenyl-3-butenyl]-4-methylvaleramide in 10 ml of methanol was hydrogenated for 3 hours in the presence of 0.02 g of 10% palladium-on-carbon. The catalyst was removed by filtration and evaporation of the solvent gave 0.120 g of N-(1,2,3,5,6,7,8,8a(RS)-octahydro-1,3-dioxoimidazo[1,5-a]pyrazin-2-yl)-2(R)-[1(S)-(hydroxycarbamoyl)-4-phenylbutyl]-4-methylvaleramide in the form of a white solid.

Workup

  1. customThe catalyst was removed by filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-d0c1e5f183134a05ab6a839bcd639b58
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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