Ethyl bromopyruvate → (2S,4R)-2-(4-carboxythiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine

HRID 37275

반응식

HRID 37275 반응식
[CH3:1][S:2]([O: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](=[S:26])[NH2:25])[CH2:7]1)(=[O:4])=[O:3].Br[CH2:28][C:29](=O)[C:30]([O:32]CC)=[O:31]>ClCCl.C(O)C>[C:30]([C:29]1[N:25]=[C:24]([C@@H:8]2[CH2:7][C@@H:6]([O:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][N:9]2[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])[S:26][CH:28]=1)([OH:32])=[O:31]

참가 물질

5

반응물 2

HCID 66144Ethyl bromopyruvateHCID 14305069(2S, 4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-thiocarbamoylpyrrolidine

생성물 1

HCID 18638791(2S,4R)-2-(4-carboxythiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S, 4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) -2-thiocarbamoylpyrrolidine (2.0 g) in dichloromethane (40 ml) was added a solution of ethyl bromopyruvate (1.04 ml) in absolute ethanol (10 ml) at 0° C. After stirring at room temperature for 2 hours, the mixture was evaporated. The residue was dissolved in ethyl acetate, and washed with saturated sodium bicarbonate and brine successively. The dried organic layer was evaporated and the residue was dissolved in tetrahydrofuran (15 ml) and in sodium hydroxide (15 ml). After stirring at 35°-45° C. for 1 hour, the mixture was evaporated and poured into ethyl acetate. To this mixture was added 1N hydrochloric acid (20 ml), and then organic layer was separated, and washed with brine. The dried organic layer was evaporated to give (2S,4R)-2- (4-carboxythiazol-2-yl)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl) pyrrolidine (1.54 g).

후처리

  1. customthe mixture was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine successively
  4. customThe dried organic layer was evaporated
  5. dissolutionthe residue was dissolved in tetrahydrofuran (15 ml) and in sodium hydroxide (15 ml)
  6. stirringAfter stirring at 35°-45° C. for 1 hour
  7. customthe mixture was evaporated
  8. additionpoured into ethyl acetate
  9. additionTo this mixture was added 1N hydrochloric acid (20 ml)
  10. customorganic layer was separated
  11. washwashed with brine
  12. customThe dried organic layer was evaporated

출처 및 근거

ORD 기록
ord-c3c1e6e1d11342b5b94ca9c31e1f536d
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420122

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