Potassium Carbonate → (S)-2-acetylthio-3-phenylpropanoic acid

HRID 233368

반응식

HRID 233368 반응식
[C:1]([OH:4])(=[S:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14]>O.[OH-].[Na+]>[C:1]([S:3][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:4])[CH3:2]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 11746403(R)-2-Bromo-3-phenylpropionic acidHCID 178418634HCID 178418634, 화합물

생성물 1

HCID 10176891(S)-2-acetylthio-3-phenylpropanoic acid수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 14798Sodium Hydroxide용매

실험 절차

Thioacetic acid (9.3 cc) and potassium carbonate (7.5 g) in water (150 cc) are added under nitrogen atmosphere to a solution of (R)-2-bromo-3-phenylpropanoic acid (25 g) in 1M sodium hydroxide (110 cc). The solution is stirred for 15 hours at a temperature close to 20° C. After evaporation under reduced pressure, the residue is taken up with water and ethyl acetate. The aqueous phase is separated, acidified to pH=2 and then extracted with ethyl acetate. After washing, the organic phase is dried over sodium sulphate. After filtration and concentration under reduced pressure, (S)-2-acetylthio-3-phenylpropanoic acid (18.5 g) is obtained with a yield of 75% in the form of an oil having the following characteristics: Rf =0.49 [hexane/ethyl acetate/acetic acid (6:4:0.5 by volume)].

후처리

  1. customclose to 20° C
  2. customAfter evaporation under reduced pressure
  3. customThe aqueous phase is separated
  4. extractionextracted with ethyl acetate
  5. washAfter washing
  6. dry with materialthe organic phase is dried over sodium sulphate
  7. filtrationAfter filtration and concentration under reduced pressure

출처 및 근거

ORD 기록
ord-13b55e1b2b834161b949f5f276cd2f4e
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591891

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