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

HRID 5101

반응식

HRID 5101 반응식
Cl.C(OC([N:9]1[CH2:13][C@@H:12]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:11][C@H:10]1[C:24](=[O:28])[NH:25][CH2:26][CH3:27])=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:26]([NH:25][C:24]([C@@H:10]1[CH2:11][C@H:12]([S:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[CH2:13][NH:9]1)=[O:28])[CH3:27]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 14880290(2S, 4S)-1-t-Butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

생성물 1

HCID 14880286(2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine수율 82.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

41.19 ml of a 4N ethyl acetate solution of hydrogen chloride were added to a solution of 13.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 100 ml of ethyl acetate, and the mixture was stirred at room temperature for 3 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 aqueous layer was saturated with ammonium chloride and extracted with tetrahydrofuran. The combined extracts were 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 (eluted with a 87:13 by volume mixture of ethyl acetate and methanol) to afford 8.00 g of the title compound as pale brown crystals, melting at 67°-68° C.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionextracted with tetrahydrofuran
  3. washThe combined extracts were washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. washeluted with a 87:13 by volume mixture of ethyl acetate and methanol)

출처 및 근거

ORD 기록
ord-b7a72d018267442bb83530e1ef42bd9e
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05242914

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