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Triethylamine → (2S,4R)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinyl carbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 727683
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HRID 727683 반응식
C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C.[OH:18][C@H:19]1[CH2:23][N:22]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=2)=[O:25])[C@H:21]([C:37]([OH:39])=O)[CH2:20]1.Cl.Cl.[N+:42]([C:45]1[CH:63]=[CH:62][C:48]([CH2:49][O:50][C:51]([O:53][CH2:54][CH2:55][N:56]2[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)=[O:52])=[CH:47][CH:46]=1)([O-:44])=[O:43]>CN(C)C=O.C(OCC)(=O)C>[OH:18][C@H:19]1[CH2:23][N:22]([C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=2)=[O:25])[C@H:21]([C:37]([N:59]2[CH2:60][CH2:61][N:56]([CH2:55][CH2:54][O:53][C:51]([O:50][CH2:49][C:48]3[CH:62]=[CH:63][C:45]([N+:42]([O-:44])=[O:43])=[CH:46][CH:47]=3)=[O:52])[CH2:57][CH2:58]2)=[O:39])[CH2:20]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 10566895trans-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-prolineHCID 675853301-[2-(4-Nitrobenzyloxycarbonyloxy)ethyl]piperazine dihydrochloride

생성물 1

HCID 22881632(2S,4R)-4-hydroxy-2-{4-[2-(4-nitrobenzyloxycarbonyl)oxyethyl]-1-piperazinyl carbonyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
수율 94.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

25.7 ml of diethyl cyanophosphonate and 68.7 ml of triethylamine were added dropwise, whilst ice-cooling, to a suspension of 47.8 g of trans-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)-L-proline and 64.8 g of 1-[2-(4-nitrobenzyloxycarbonyloxy)ethyl]piperazine dihydrochloride in 400 ml of dry dimethylformamide, and the resulting mixture was stirred at the same temperature for 30 minutes. At the end of this time, the reaction mixture was diluted with 1.5 liters of ethyl acetate, and the dilute solution was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, to give 87.6 g of the title compound, as a powder.

후처리

  1. washthe dilute solution was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-38f9856a613b4dd5960f1c0a62f1d5f4
출처 데이터셋
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05712267

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