HCID 86757294, compound → HCID 86757293, compound

HRID 651785Notes

Reaction equation

HRID 651785 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:22]([NH:24][N:25]1[C:30](=[O:31])[CH2:29][N:28](C(OCC2C=CC=CC=2)=O)[CH2:27][C:26]1=[O:42])=[O:23])[CH2:12][CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]>C(O)(C)C.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:43][CH:44]([CH3:46])[CH3:45])[C:22]([NH:24][N:25]1[C:26](=[O:42])[CH2:27][NH:28][CH2:29][C:30]1=[O:31])=[O:23])[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

4

Reactant 1

HCID 86757294HCID 86757294, compound

Product 1

HCID 86757293HCID 86757293, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 0.178 g of 2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-4-methyl-N-(4-benzyloxycarbonyl-2,6-dioxo-1-piperazinyl)valeramide in 5 ml of isopropyl alcohol was hydrogenated for 4 hours in the presence of 0.020 g of 10% palladium-on-carbon. The catalyst was removed by filtration and the solvent was evaporated to give 0.072 g of 2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenylbutyl]-4-methyl-N-(2,6-dioxo-1-piperazinyl)valeramide in the form of a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5a807ba874464603a869f93992671368
Source dataset
uspto-grants-2001_08
Patent number
US06281363B1

Reaction notes

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