Hydrochloric Acid → (3R)-2-(4-chloro-2-methylphenyl)-4,4,4-trifluoro-3-methylbutanoic acid

HRID 1476112노트

반응식

HRID 1476112 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C@@H:14]([CH3:19])[C:15]([F:18])([F:17])[F:16])[C:9]([O:11]CC)=[O:10])=[C:4]([CH3:20])[CH:3]=1.Cl>CO.C1COCC1.O.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C@@H:14]([CH3:19])[C:15]([F:16])([F:17])[F:18])[C:9]([OH:11])=[O:10])=[C:4]([CH3:20])[CH:3]=1

참가 물질

7

반응물 2

HCID 313Hydrochloric AcidHCID 58288191Ethyl(3R)-2-(4-chloro-2-methylphenyl)-4,4,4-trifluoro-3-methylbutanoate

생성물 1

HCID 58288205(3R)-2-(4-chloro-2-methylphenyl)-4,4,4-trifluoro-3-methylbutanoic acid

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 14798Sodium Hydroxide용매

실험 절차

3.10 g (crude, about 10.04 mmol) of ethyl (3R)-2-(4-chloro-2-methylphenyl)-4,4,4-trifluoro-3-methylbutanoate (diastereomer mixture) were dissolved in a mixture of 10 ml of methanol, 10 ml of THF and 5 ml of water, and 8.03 g of 50% strength aqueous sodium hydroxide solution were added at 0° C. The reaction mixture was stirred at RT overnight. The mixture was then acidified with 1 N hydrochloric acid (pH about 2) and extracted three times with ethyl acetate. The combined organic phases were washed with sat. sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1 to 4:1). This gave 1.46 g (51.8% of theory) of the target product as a mixture of diastereomers (about 5:1).

후처리

  1. additionwere added at 0° C
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases were washed with sat. sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1 to 4:1)
  7. additionThis gave 1.46 g (51.8% of theory) of the target product as a mixture of diastereomers (about 5:1)

출처 및 근거

ORD 기록
ord-cce49ecfb94643f0b88de50fa29fdca5
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018414B2

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