2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvaleric acid → 2(R)-[1(S)-(tert-butoxycarbonyl)-4-cyclohexylbutyl]-4-methylvaleric acid

HRID 1978071Notes

Reaction equation

HRID 1978071 reaction equation
[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:19]([OH:21])=[O:20])[CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pt]=O>[C:1]([O:5][C:6]([C@H:8]([C@@H:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:19]([OH:21])=[O:20])[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 153807642(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvaleric acid

Product 1

HCID 206580082(R)-[1(S)-(tert-butoxycarbonyl)-4-cyclohexylbutyl]-4-methylvaleric acidYield 65.9%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1.0 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-phenylbutyl]-4-methylvaleric acid in 30 ml of acetic acid was hydrogenated over 300 mg of platinum oxide for 1.5 hours. The catalyst was removed by filtration and the solvent was evaporated. Final traces of acetic acid were removed by the addition and evaporation of toluene (3×10 ml). Chromatography on silica gel using diethyl ether/hexane (1:7) for the elution followed by evaporation yielded 0.67 g of 2(R)-[1(S)-(tert-butoxycarbonyl)-4-cyclohexyl-butyl]-4-methylvaleric acid as a white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated
  3. customwere removed by the addition and evaporation of toluene (3×10 ml)
  4. washfor the elution
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-3287991b9d5b4b9288d6b89627e18418
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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