Boron trifluoride etherate → (2S,4S)-4-acetylthio-2-(1,3-dithiolan-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 846942

반응식

HRID 846942 반응식
[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH:23]=O)[CH2:6]1)(=[O:3])[CH3:2].[CH2:25]([SH:28])[CH2:26][SH:27].B(F)(F)F.CCOCC.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)=[O:11])[C@H:7]([CH:23]2[S:28][CH2:25][CH2:26][S:27]2)[CH2:6]1)(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 516892Sodium BicarbonateHCID 18638815(2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

생성물 1

HCID 57182042(2S,4S)-4-acetylthio-2-(1,3-dithiolan-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,4S)-4-acetylthio-2-formyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (1.00 g) and 1,2-ethanedithiol (0.36 ml) in dichloromethane (20 ml) was added boron trifluoride etherate (0.1 ml), and the solution was stirred for 14 hours at ambient temperature. To the mixture was added saturated aqueous sodium hydrogen carbonate and the organic layer was separated, and washed with brine. The organic layer was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (50 ml) and eluted with a mixture of acetone and dichloromethane (2:98, V/V) to give (2S,4S)-4-acetylthio-2-(1,3-dithiolan-2-yl)-1-(4 -nitrobenzyloxycarbonyl)pyrrolidine (1.14 g).

후처리

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (50 ml)
  6. washeluted with a mixture of acetone and dichloromethane (2:98, V/V)

출처 및 근거

ORD 기록
ord-ac4cafffe8f64141bd4913a57cac9332
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05138064

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