Sodium Hydroxide → (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid

HRID 1610724ノート

反応式

HRID 1610724 の反応式
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[CH2:8][CH:9]([CH:15]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[OH:16])[C:10]([O:12]CC)=[O:11])([F:4])[CH3:3].[OH-].[Na+]>O1CCCC1CCO>[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[CH2:8][CH:9]([CH:15]([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)[OH:16])[C:10]([OH:12])=[O:11])([F:4])[CH3:3]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 86593306ethyl (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionate

生成物 1

HCID 22261533(2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid収率 82%

試薬・触媒・溶媒 1

HCID 119895722-(Oxolan-2-yl)ethan-1-ol溶媒

実験手順

To a solution of ethyl (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionate (5.97 g, 17.6 mmol) in tetrahydrofuran-ethanol (30 ml)-(20 ml) was added 2N sodium hydroxide (18 ml, 36 mmol) at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure, and the aqueous layer was acidified with 1N hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The filtrate was recrystallized from hexane-ethyl acetate to give (2RS,3RS)-2-[3-(1,1-difluoroethyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid(4.48 g, 82%) as colorless crystals.

後処理

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe filtrate was recrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-f103aa0a97e247948d3ddcf6afd6e7ad
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

反応ノート

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