Hydrochloric Acid → (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioic acid

HRID 888232ノート

反応式

HRID 888232 の反応式
[OH:1][C@@H:2]([C@@H:9]([CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1)[C:10]([O:12]C(C)C)=[O:11])[C:3]([O:5]C(C)C)=[O:4].[OH-].[K+].Cl>C1COCC1.O>[OH:1][C@@H:2]([C@@H:9]([CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:23][CH:24]=1)[C:10]([OH:12])=[O:11])[C:3]([OH:5])=[O:4]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58487998diisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioate

生成物 1

HCID 58487990(2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioic acid収率 110.9%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a solution of diisopropyl (2S,3R)-2-hydroxy-3-{3-[4-(trifluoromethoxy)phenyl]propyl}butanedioate (6.98 g; 16.6 mmol; 1.0 eq.) in THF/water (3/1; 140 mL) was added potassium hydroxide (5.59 g; 99.6 mmol; 6.0 eq.). The reaction mixture was then stirred for 14 h at RT. The aq. layers were acidified with an aqueous solution of HCl to pH 2, extracted with EtOAc. The combined organic layers were then dried over MgSO4 and evaporated to give the title compound as an oil (6.19 g), used in the next steps without further purification.

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were then dried over MgSO4
  3. customevaporated

出典と根拠

ORDレコード
ord-b4339f150c964837b0dec952608075ce
出典データセット
uspto-grants-2012_08
特許番号
US08247437B2

反応ノート

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