Dimethylformamide dimethyl acetal → (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(1,2,4-thiadiazol-5-yl)pyrrolidine

HRID 846927

反応式

HRID 846927 の反応式
[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].CO[CH:29](OC)[N:30](C)C>>[CH3:1][S:2]([O: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]2[S:26][N:30]=[CH:29][N:25]=2)[CH2:7]1)(=[O:4])=[O:3]

参加物

3

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 14305069(2S, 4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-thiocarbamoylpyrrolidine

生成物 1

HCID 57267420(2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(1,2,4-thiadiazol-5-yl)pyrrolidine

実験手順

To (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-thiocarbamoylpyrrolidine (1.5 g) was added N,N-dimethylformamide dimethylacetal (1.5 ml) and the mixture was stirred at room temperature for 1.5 hours. After the solvent was removed, the residue was dissolved in dichloromethane (30 ml). To the solution was added dropwise O-(mesitylenesulfonyl)hydroxylamine (1.5 g) in dichloromethane (20 ml) at 0° C. After stirring at room temperature for 2 hours, the mixture was washed with saturated aqueous sodium bicarbonate and brine successively. The dried organic layer was evaporated and the residue was subjected to a column chromatography on silica gel (30 g) eluting with a mixture of n-hexane and ethyl acetate (1:2 V/V) to give (2S,4R)-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)-2-(1,2,4-thiadiazol-5-yl)pyrrolidine (850 mg).

後処理

  1. customAfter the solvent was removed
  2. dissolutionthe residue was dissolved in dichloromethane (30 ml)
  3. additionTo the solution was added dropwise O-(mesitylenesulfonyl)hydroxylamine (1.5 g) in dichloromethane (20 ml) at 0° C
  4. stirringAfter stirring at room temperature for 2 hours
  5. washthe mixture was washed with saturated aqueous sodium bicarbonate and brine successively
  6. customThe dried organic layer was evaporated
  7. washeluting with a mixture of n-hexane and ethyl acetate (1:2 V/V)

出典と根拠

ORDレコード
ord-0dbc7b47e1e448e2b4a219ad357c6f54
出典データセット
uspto-grants-1992_08
特許番号
US05138064

関連ノート

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