3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid methylamide → (2RS,4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-octanoic acid methylamide

HRID 232136Notes

Reaction equation

HRID 232136 reaction equation
[CH3:1][NH:2][C:3](=[O:36])[C:4]([CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)=[CH:5][C@@H:6]1[O:10]C(C)(C)[N:8](C(OCC2C=CC=CC=2)=O)[C@H:7]1[CH2:23][CH:24]([CH3:26])[CH3:25]>C(O)C.[Pd]>[CH3:1][NH:2][C:3](=[O:36])[CH:4]([CH2:27][CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[CH2:5][C@H:6]([OH:10])[C@@H:7]([NH2:8])[CH2:23][CH:24]([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 700461233-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid methylamide

Product 1

HCID 57159732(2RS,4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-octanoic acid methylamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

29.2 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)ethyl]-2-propenoic acid methylamide was dissolved in ethanol and then hydrogenated by using palladium black as a catalyst under atmospheric pressure. The reaction mixture was subjected to filtration, and the solvent of the filtrate was distilled off under reduced pressure to obtain 19.2 mg of (2RS,4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-octanoic acid methylamide.

Workup

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

Sources & evidence

ORD record
ord-ed1b58663ef845cf9671545d2c991595
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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