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

HRID 1978071ノート

反応式

HRID 1978071 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3287991b9d5b4b9288d6b89627e18418
出典データセット
uspto-grants-2001_05
特許番号
US06235787B1

反応ノート

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