HCID 57056538, compound → HCID 57316905, compound

HRID 232134Notes

Reaction equation

HRID 232134 reaction equation
[CH2:1]([NH:5][C:6](=[O:40])[C:7]([CH2:30][CH:31]([O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1)[CH3:32])=[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].[H][H]>C(O)C.[Pd]>[CH2:1]([NH:5][C:6](=[O:40])[CH:7]([CH2:30][CH:31]([O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1)[CH3:32])[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

5

Reactant 2

HCID 57056538HCID 57056538, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57316905HCID 57316905, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

254 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-4-isobutyl-2,2-dimethyloxazolidin-5-yl]-2-[2-(2-tetrahydropyranyloxy)propyl]-2-propenoic acid isobutylamide was dissolved in 3 ml of ethanol. Then, a palladium black catalyst was added thereto, and hydrogen was continuously blown into the solution under atmospheric pressure for 4 hours. Then, the catalyst was filtered off, and a fresh palladium black catalyst was added. Then, hydrogen was continuously brown into the solution for further 4 hours. The catalyst was filtered off, and the reaction solution was concentrated and dried under reduced pressure to obtain 180 mg of (2RS,4S,5S)-5-amino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)propyl]-7-methyl-octanoic acid isobutylamide as a solid substance.

Workup

  1. filtrationThen, the catalyst was filtered off
  2. additiona fresh palladium black catalyst was added
  3. filtrationThe catalyst was filtered off
  4. concentrationthe reaction solution was concentrated
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-8f6156fd8fb349f7bdb9fa910653a645
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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