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

HRID 5068

반응식

HRID 5068 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5a57398a5c504dffb529c848afe88765
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

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