反応 #11024

ord-908bddf74474441f8443475f190a40a2

反応方程式

CC([O-])=S.[K+]
Potassium thioacetate
O=C(O)[C@H](Cl)Cc1ccccc1
(2R)-2-chloro-3-phenylpropionic acid
O=S([O-])([O-])=S.[Na+].[Na+]
sodium thiosulfate
CC(=O)S[C@@H](Cc1ccccc1)C(=O)O
(2S)-2-acetylthio-3-phenylpropionic acid
収率 83.4%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    抽出the whole mixture was extracted with 30 ml of ethyl acetate
  2. 2
    洗浄The organic phase was washed with 3 ml of 6% sodium thiosulfate aqueous solution, 3 ml of water and 3 ml of a saturated aqueous solution of sodium chloride
  3. 3
    乾燥dried over sodium sulfate
  4. 4
    その他The solvent was removed under reduced pressure

実験手順

Potassium thioacetate (68 mg, 0.64 mmol) was added to a solution of 100 mg (0.54 mmol) of the (2R)-2-chloro-3-phenylpropionic acid obtained in Example 14 in 2 ml of dimethylformamide at room temperature, and the mixture was stirred for 24 hours. A 6% aqueous solution of sodium thiosulfate (0.5 ml) was added to the reaction mixture, and the whole mixture was extracted with 30 ml of ethyl acetate. The organic phase was washed with 3 ml of 6% sodium thiosulfate aqueous solution, 3 ml of water and 3 ml of a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. The solvent was removed under reduced pressure to give 101 mg (yield 83%) of the desired (2S)-2-acetylthio-3-phenylpropionic acid.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07094926B2uspto-grants-2006_08