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

HRID 727683Notes

Reaction equation

HRID 727683 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-38f9856a613b4dd5960f1c0a62f1d5f4
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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