HCID 57270466, compound → HCID 57111561, compound

HRID 1651020Notes

Reaction equation

HRID 1651020 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.[C].[Pd]>[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]([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 57111561HCID 57111561, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

216 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid isobutylamide was dissolved in 2.1 ml of ethanol, and hydrogenated by using 10% palladium carbon under atmospheric pressure. The reaction mixture was subjected to filtration, and the solvent was distilled off from the filtrate under reduced pressure to obtain 124 mg of (4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octenoic 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-1078d514c16f4c469d394399aa5a7c36
Source dataset
uspto-grants-1990_05
Patent number
US04927565

Reaction notes

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