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

HRID 1677791노트

반응식

HRID 1677791 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-05fb61a5b3614ca4a263b44d52a6e2f8
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008302B2

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