Iodoethane → (2S, 4S)-2-Carbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

HRID 5096

反応式

HRID 5096 の反応式
[CH2:1](I)[CH3:2].C(=O)(O)[O-].[Na+].[C:9]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14][NH:13]1)(=[O:11])[NH2:10]>CN(C)C=O>[C:9]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:14][N:13]1[CH2:1][CH3:2])(=[O:11])[NH2:10]

参加物

5

反応物 3

HCID 6340IodoethaneHCID 516892Sodium Bicarbonate2 回HCID 14880267(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

生成物 1

HCID 14796650(2S, 4S)-2-Carbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.362 ml of ethyl iodide and 315 mg of sodium bicarbonate to a solution of 1000 mg of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 10 ml of dry dimethylformamide were added, whilst ice-cooling, and the mixture was stirred at room temperature for 5.5 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through silica gel (Katayama Chemicals Co., Silica Gel 60K070) and 560 mg of the title compound were obtained as crystals, melting at 124°-125° C., from the fractions eluted with ethyl acetate.

後処理

  1. additionwere added, whilst ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-ad59de36260c4266b878a79c69cfa272
出典データセット
uspto-grants-1993_09
特許番号
US05242914

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