Thioacetic acid → (2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine

HRID 1650842노트

반응식

HRID 1650842 반응식
[H-].[Na+].[C:3]([SH:6])(=[O:5])[CH3:4].CS(O[C@H:12]1[CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C@H:14]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([CH3:36])[C:32]2=[O:37])[CH2:13]1)(=O)=O>CN(C)C=O>[C:3]([S:6][C@@H:12]1[CH2:16][N:15]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:18])[C@H:14]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([CH3:36])[C:32]2=[O:37])[CH2:13]1)(=[O:5])[CH3:4]

참가 물질

5

반응물 3

HCID 10484Thioacetic acidHCID 24758Sodium hydrideHCID 15056144HCID 15056144, 화합물

생성물 1

HCID 15056145(2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of sodium hydride (0.35 g) in N,N-dimethylformamide (30 ml) was added dropwise thioacetic S-acid (0.74 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. A solution of (2S,4R)-4-methanesulfonyloxy-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (3.17 g) in N,N-dimethylformamide (7 ml) was added to the mixture obtained above with stirring at the same temperature. The mixture was stirred at 80°-90° C. for 2 hours. The reaction mixture was poured into ice-water (100 ml) and extracted twice with ethyl acetate (100 ml). The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-4-acetylthio-2-(3-methyl-2-oxoimidazolidin-1-yl)methyl-1(4 -nitrobenzyloxycarbonyl)pyrrolidine (1.74 g).

후처리

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. customobtained above
  4. stirringwith stirring at the same temperature
  5. stirringThe mixture was stirred at 80°-90° C. for 2 hours
  6. extractionextracted twice with ethyl acetate (100 ml)
  7. washThe extract was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe resulting residue was chromatographed on silica gel (100 g)
  11. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  12. additionThe fractions containing the desired compound
  13. customwere collected
  14. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-98033dee3d4646939aaa88ea173aca0b
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04925838

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