Hydrochloric Acid → (2R,4S)-4-Mercapto-2-[4-[2-(4-nitrobenzyloxycarbonyl) oxyethyl]-1-piperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 362078노트

반응식

HRID 362078 반응식
Cl.C([S:5][C@@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[O:12])[C@@H:8]([C:24]([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][O:34][C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=3)=[O:36])[CH2:28][CH2:27]2)=[O:25])[CH2:7]1)(=O)C>>[SH:5][C@@H:6]1[CH2:10][N:9]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=2)=[O:12])[C@@H:8]([C:24]([N:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH2:33][O:34][C:35]([O:37][CH2:38][C:39]3[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=3)=[O:36])[CH2:30][CH2:31]2)=[O:25])[CH2:7]1

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 86753700(2R,4S)-4-acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

생성물 1

HCID 22881631(2R,4S)-4-Mercapto-2-[4-[2-(4-nitrobenzyloxycarbonyl) oxyethyl]-1-piperazinylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine수율 60.5%

실험 절차

40 ml of a 10% w/v methanolic solution of hydrogen chloride were added to a solution of 1.0 g of (2R,4S)-4-acetylthio-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinylcarbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine [prepared as described in step (ii) above] in 10 ml of 1,4-dixoane, and the resulting mixture was stirred at 50° C. to 52° C. for 1 hour. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the concentrate was diluted with 100 ml of ethyl acetate. The dilute solution was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and washed, in turn, with 30 ml of water and with 30 ml of an aqueous solution of sodium chloride. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 566 mg of the title compound, as a colorless powder.

후처리

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. additionthe concentrate was diluted with 100 ml of ethyl acetate
  3. washwashed, in turn, with 30 ml of water and with 30 ml of an aqueous solution of sodium chloride
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and methanol as the eluent

출처 및 근거

ORD 기록
ord-845726088c124627be6dab09c953ae12
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866564

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