Ethyl Acetate → (S)-3-(3-Bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid

HRID 1432107노트

반응식

HRID 1432107 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9]Br)[CH:3]=1.C([S:14][CH2:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18])(=O)C.[OH-].[Na+].CCOC(C)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[CH2:9][S:14][CH2:15][C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2724506D-beta-acetylthioisobutyric acidHCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene

생성물 1

HCID 68541731(S)-3-(3-Bromo-5-methyl-benzylsulfanyl)-2-methyl-propionic acid

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 5.55 g (21 mmol) 1-bromo-3-bromomethyl-5-methyl-benzene and 2.90 ml (21 mmol) (S)-3-acetylsulfanyl-2-methyl-propionic acid in 32 ml methanol is cooled in an ice bath and 4N aqueous sodium hydroxide (15.8 ml, 63 mmol) are added. The reaction mixture is stirred at rt for 3 hrs. EtOAc is added to the mixture and the organic layer is washed with water and brine and evaporated. Filtration over silica gel (flashmaster, hexane to hexane/EtOAc 4/6) gives the title compound.

후처리

  1. washthe organic layer is washed with water and brine
  2. customevaporated
  3. filtrationFiltration over silica gel (flashmaster, hexane to hexane/EtOAc 4/6)

출처 및 근거

ORD 기록
ord-25d74e1d243940ddb7790c5ebb43d38c
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612055B2

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