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

HRID 1476112ノート

反応式

HRID 1476112 の反応式
[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

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cce49ecfb94643f0b88de50fa29fdca5
出典データセット
uspto-grants-2015_04
特許番号
US09018414B2

反応ノート

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