Water → (2R)-chloro-3-phenylpropionic acid

HRID 10923

반응식

HRID 10923 반응식
S(Cl)([Cl:3])=O.O[C@@H:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8].O>O1CCCC1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:3][C@H:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8]

참가 물질

6

반응물 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 4447183-Phenyllactic acid, (S)-

생성물 1

HCID 11458104(2R)-chloro-3-phenylpropionic acid수율 90.1%

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

Thionyl chloride (0.66 ml, 9.0 mmol) was added dropwise to a solution of (2S)-2-hydroxy-3-phenylpropionic acid (500 mg, 3.0 mmol, optical purity 100% ee (S)) in 5 ml of tetrahydrofuran at room temperature, and the mixture was stirred for 15 hours. To the reaction mixture was added 170 mg (0.60 mmol) of tetra-n-butylammonium chloride, and the mixture was heated at 40° C. for 4 hours. Water (5 ml) was added to the reaction mixture and, after 30 minutes of stirring, the mixture was extracted with 90 ml of ethyl acetate. The organic phase was washed with 10 ml of a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 499 mg (yield 90%) of the desired (2R)-chloro-3-phenylpropionic acid.

후처리

  1. stirringof stirring
  2. extractionthe mixture was extracted with 90 ml of ethyl acetate
  3. washThe organic phase was washed with 10 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-f826208111eb48df98d017f97031333a
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094926B2

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