Potassium Persulfate → (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionic acid

HRID 275594

反応式

HRID 275594 の反応式
C1CCN2C(=NCCC2)CC1.S[C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15].[CH2:19]([C:26](=[CH2:37])[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[S:38]([O:42]OS([O-])(=O)=O)([O-])(=O)=[O:39].[K+].[K+]>O>[CH2:30]([O:29][C:27]([CH:26]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:37][S:38]([C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=[O:15])(=[O:42])=[O:39])=[O:28])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

6

反応物 4

HCID 24412Potassium Persulfate2 回HCID 784212-Mercapto-2-methylpropanoic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10912012Benzyl 2-Benzylacrylate

生成物 1

HCID 20088400(RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

8.4 g (55.4 mm01) of DBU were added dropwise to a solution of 3.3 g (27.7 mmol) of 2-mercaptoisobutyric acid [Can. J. Chem. 61(8), 1872]and 6.9 g (27.7 mmol) of benzyl 2-benzylacrylate (EPA 0117429), whereby the temperature of the reaction mixture was held between 5 and 10°. After completion of the addition the mixture was stirred at 10° for a further 5 hours. Subsequently, the reaction mixture was treated dropwise with 22.5 g (36.6 mmol) of potassium monopersulphate triple salt suspended in 450 ml of water while cooling with ice, whereby the temperature was held below 10°. Thereafter, the mixture was stirred at the same temperature for a further hour, then cooled to 0° and a further 22.5 g (36.6 mmol) of potassium monopersulphate triple salt were added spatula-wise. The mixture was left to warm slowly to room temperature and was stirred for a further 15 hours. For the working-up, the mixture was diluted with 200 ml of water and extracted four times with 60 ml of ethyl acetate each time. The combined organic extracts were dried over sodium sulphate and evaporated under reduced pressure until the product began to crystallize. Then, 30 ml of hexane and 20 ml of ether were added while stirring, the separated product was subsequently filtered off under suction and dried. There were obtained 9.7 g of (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionic acid as a colourless solid; MS: 422 (M+NH4)+.

後処理

  1. customwas held between 5 and 10°
  2. additionAfter completion of the addition the mixture
  3. temperaturewhile cooling with ice, whereby the temperature
  4. customwas held below 10°
  5. stirringThereafter, the mixture was stirred at the same temperature for a further hour
  6. temperaturecooled to 0°
  7. waitThe mixture was left
  8. stirringwas stirred for a further 15 hours
  9. extractionextracted four times with 60 ml of ethyl acetate each time
  10. dry with materialThe combined organic extracts were dried over sodium sulphate
  11. customevaporated under reduced pressure until the product
  12. customto crystallize
  13. additionThen, 30 ml of hexane and 20 ml of ether were added
  14. stirringwhile stirring
  15. filtrationthe separated product was subsequently filtered off under suction
  16. customdried

出典と根拠

ORDレコード
ord-505f7d4ad3c24960bd0f29a0bf5f48d3
出典データセット
uspto-grants-1995_02
特許番号
US05393875

関連ノート

読み込み中…