HCID 57270466, compound → HCID 57316415, compound

HRID 232131Notes

Reaction equation

HRID 232131 reaction equation
[CH2:1]([NH:5][C:6](=[O:39])[C:7]([CH2:30][CH2:31][O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)=[CH:8][C@@H:9]1[O:13]C(C)(C)[N:11](C(OCC2C=CC=CC=2)=O)[C@H:10]1[CH2:26][CH:27]([CH3:29])[CH3:28])[CH:2]([CH3:4])[CH3:3]>C(O)C.[Pd]>[CH2:1]([NH:5][C:6](=[O:39])[CH:7]([CH2:30][CH2:31][O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH2:8][C@H:9]([OH:13])[C@@H:10]([NH2:11])[CH2:26][CH:27]([CH3:29])[CH3:28])[CH:2]([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 57270466HCID 57270466, compound

Product 1

HCID 57316415HCID 57316415, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

101 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid isobutylamide in 1 ml of ethanol and hydrogenated by using palladium black under atmospheric pressure. The reaction mixture was subjected to filtration, and the solvent was distilled off from the filtrate under reduced pressure to obtain 64 mg of (2RS,4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-octanoic acid isobutylamide as a colorless oily substance.

Workup

  1. filtrationThe reaction mixture was subjected to filtration
  2. distillationthe solvent was distilled off from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c32a3a89557a4b549ae53f0f7cf5b545
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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