Hydrochloric Acid → (2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

HRID 1030131ノート

反応式

HRID 1030131 の反応式
C(OC([N:8]1[CH2:12][C@@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23](=[O:25])[NH2:24])=O)(C)(C)C.O1CCOCC1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:23]([C@@H:9]1[CH2:10][C@H:11]([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:12][NH:8]1)(=[O:25])[NH2:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 14880265(2S, 4S)-1-(t-butoxycarbonyl)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine

生成物 1

HCID 14880267(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine収率 97.5%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

1.92 g of (2S, 4S)-1-(t-butoxycarbonyl)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] was dissolved in 25 ml of ethyl acetate, and 26.2 ml of a 4N dioxane solution of hydrogen chloride were added to the solution, whilst ice-cooling. The mixture was then stirred at 0° to 5° C. for 2 hours and at room temperature for 30 minutes. At the end of this time, it was poured into a saturated aqueous solution of sodium bicarbonate, to make it weakly basic, and was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.36 g of the title compound as a powder, melting at 120°-121° C.

後処理

  1. temperaturecooling
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure

出典と根拠

ORDレコード
ord-ba4569551baf46c690fc02dcd6230f62
出典データセット
uspto-grants-1992_04
特許番号
US05104867

反応ノート

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