Triethyl phosphonoacetate → HCID 57102019, compound

HRID 648662Notes

Reaction equation

HRID 648662 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[N:17]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH:29]([CH:33]([C:42]([NH2:44])=[O:43])[C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)[CH2:30][CH2:31][CH3:32])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C)C=O>[N:17]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH:29]([CH:33]([C:42]([NH2:44])=[O:43])[C:34]2[CH:35]=[CH:36][C:37]([CH:38]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:40][CH:41]=2)[CH2:30][CH2:31][CH3:32])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 20145125HCID 20145125, compound

Product 1

HCID 57102019HCID 57102019, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2.80 gm (12.5 m mol) of ethyl diethylphosphonoacetate in 10 ml of absolute dimethylformamide was added dropwise, at ambient temperature, to 0.60 gm (12.5 m mol) of sodium hydride (50% in oil) in 15 ml of absolute dimethylformamide. The mixture was stirred for 15 minutes (until the development of gas ceased), and then a solution of 2.4 gm (6.34 m mol) of 4-[(1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-benzaldehyde in 10 ml of absolute dimethylformamide was added thereto dropwise. The mixture was stirred for two hours at ambient temperature, concentrated by evaporation in vacuo, and distributed between water and ether. The ether phase was dried, filtered, and then evaporated in vacuo. The evaporation residue was purified by column chromatography on silica gel [toluene/acetone (10:1)].

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for two hours at ambient temperature
  3. concentrationconcentrated by evaporation in vacuo
  4. dry with materialThe ether phase was dried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe evaporation residue was purified by column chromatography on silica gel [toluene/acetone (10:1)]

Sources & evidence

ORD record
ord-236d84454152414b9e05e84bed76fb73
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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