Lithium Hydroxide → 5(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(p-benzyloxyphenyl)methyl]-hexanoic acid

HRID 263773ノート

反応式

HRID 263773 の反応式
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:26][CH:25]=2)[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:38].[Li+]>C(COC)OC.O>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:38])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:28][CH:29]=1)[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:6])([CH3:5])[CH3:7])=[O:2]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 156595565(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-[(p-benzyloxyphenyl)methyl]dihydrofuran-2-(3H)-one

生成物 1

HCID 228742955(S)-(Boc-Amino)-4(S)-hydroxy-6-phenyl-2(R)-[(p-benzyloxyphenyl)methyl]-hexanoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Analogously to Example 1i), 1.4 g (2.79 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-(p-benzyloxyphenylmethyl)-dihydrofuran-2-(3H)-one in 45 ml of dimethoxyethane and 23 ml of water are hydrolysed with 11 ml of 1M lithium hydroxide solution. The reaction mixture, partially concentrated by evaporation, is poured onto a mixture of ice, 137 ml of sat. NH4Cl solution, 11 ml of 10% citric acid solution and 56 ml of methylene chloride, and methanol is added until the precipitated solid has dissolved. The aqueous phase is extracted with 2 portions of methylene chloride/methanol approximately 10:1, and the organic phases are washed with brine, dried with Na2SO4 and concentrated by evaporation: tRet (II)=24.0 min; FAB-MS (M+H)+ =520.

後処理

  1. concentrationThe reaction mixture, partially concentrated by evaporation
  2. additionis poured onto a mixture of ice, 137 ml of sat. NH4Cl solution, 11 ml of 10% citric acid solution and 56 ml of methylene chloride, and methanol
  3. additionis added until the precipitated solid
  4. dissolutionhas dissolved
  5. extractionThe aqueous phase is extracted with 2 portions of methylene chloride/methanol approximately 10:1
  6. washthe organic phases are washed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated by evaporation
  9. custom(II)=24.0 min

出典と根拠

ORDレコード
ord-46f52bcef63242fe9649e07617051d50
出典データセット
uspto-grants-1997_07
特許番号
US05643878

反応ノート

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