Sodium Hydroxide → (2S,4R)-4-methanesulfonyloxy-2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37258

반응식

HRID 37258 반응식
P(Cl)(Cl)(Cl)=O.[C:6]([C@@H:9]1[CH2:13][C@@H:12]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11][N:10]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)=[O:20])(O)=[O:7].[CH3:32][NH:33][C:34](=[S:37])[NH:35][NH2:36].[OH-].[Na+]>O1CCCC1.O.CN(C)C=O>[CH3:18][S:15]([O:14][C@H:12]1[CH2:11][N:10]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)=[O:20])[C@H:9]([C:6]([NH:36][NH:35][C:34]([NH:33][CH3:32])=[S:37])=[O:7])[CH2:13]1)(=[O:17])=[O:16]

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 2723853N-MethylhydrazinecarbothioamideHCID 13502650trans-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-L-proline

생성물 1

HCID 14305077(2S,4R)-4-methanesulfonyloxy-2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine수율 81.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a mixture of dimethylformamide (2.9 ml) and tetrahydrofuran (6 ml) was dropwise added phosphorus oxychloride (2.8 ml) at -5°∫5° C. and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added a solution of (2S,4R)-2- carboxy-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (9.65 g) in tetrahydrofuran (20 ml) at -5°∫5° C., followed by stirring at the same temperature for 30 minutes. The mixture was dropwise added to a solution of 4-methylthiosemicarbazide (25 g) in a mixture of water (200 ml) and tetrahydrofuran (200 ml) at 0°-10° C. with stirring, keeping the pH between 8-9 with 1N aqueous sodium hydroxide. The mixture was stirred at the same condition for 2 hours. Tetrahydrofuran was evaporated under reduced pressure to give precipitates. The precipitates were collected by filtration, washed with water and diisopropyl ether successively, and dried over phosphorus pentoxide to give (2S, 4R)-4-methanesulfonyloxy -2-(4-methylthiosemicarbazidocarbonyl)-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (9.61 g).

후처리

  1. customat -5°
  2. custom∫5° C.
  3. stirringby stirring at the same temperature for 30 minutes
  4. stirringwith stirring
  5. stirringThe mixture was stirred at the same condition for 2 hours
  6. customTetrahydrofuran was evaporated under reduced pressure
  7. customto give
  8. customprecipitates
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with water and diisopropyl ether successively
  11. dry with materialdried over phosphorus pentoxide

출처 및 근거

ORD 기록
ord-0c8c3713669a4ab5982b2d36c3469622
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420122

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