Methyl iodide → HCID 14796652、化合物

HRID 1030132

反応式

HRID 1030132 の反応式
CI.[C:3]([C@@H:6]1[CH2:10][C@H:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:8][NH:7]1)(=[O:5])[NH2:4].[C:21](=O)(O)[O-].[Na+]>CN(C)C=O>[C:3]([C@@H:6]1[CH2:10][C@H:9]([S:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH2:8][N:7]1[CH3:21])(=[O:5])[NH2:4]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 14880267(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

生成物 1

HCID 14796652HCID 14796652、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.07 ml of methyl iodide was added, whilst ice-cooling, to a solution of 0.6 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (5) above] dissolved in 4.5 ml of dry dimethylformamide. The mixture was then stirred at 0° to 5° C. for 5 minutes and at room temperature for 20 minutes. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then the residue was subjected to column chromatography using a Lobar column (Merck, LiChroprep Si 60, size B), and 252 mg of the title compound, melting at 113°-114° C., were obtained as crystals from the fractions eluted with a 9:1 by volume mixture of ethyl acetate and methanol.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customwere obtained as crystals from the fractions
  6. washeluted with a 9:1 by volume mixture of ethyl acetate and methanol

出典と根拠

ORDレコード
ord-846d7e43ea964438b8ae1704ec66fd2b
出典データセット
uspto-grants-1992_04
特許番号
US05104867

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