Triethyl phosphonoacetate → HCID 68459285, compound

HRID 501450Notes

Reaction equation

HRID 501450 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH2:17]([N:21]1[C:25]([C:26]#[N:27])=[C:24]([CH:28]=O)[N:23]=[C:22]1[N:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1)[C:18]#[C:19][CH3:20].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:17]([N:21]1[C:25]([C:26]#[N:27])=[C:24]([CH:28]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:23]=[C:22]1[N:30]1[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35]1)[C:18]#[C:19][CH3:20]

Participants

7

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 23070760HCID 23070760, compound

Product 1

HCID 68459285HCID 68459285, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

0.038 g of sodium hydride was added to a 5 ml tetrahydrofuran solution of 0.243 g of ethyl diethylphosphonoacetate at 5° C. under a nitrogen atmosphere. 0.310 g of t-butyl 4-[1-(2-butynyl)-5-cyano-4-formyl-1H-imidazol-2-yl]piperazine-1-carboxylate dissolved in 5 ml of tetrahydrofuran was added, and the mixture was stirred for 30 minutes. 50 ml of ethyl acetate and 25 ml of 0.1N sodium hydroxide were added to the solution. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 0.380 g of the title compound was obtained from the fraction eluted with ethyl acetate-hexane (3:7).

Workup

  1. additionwas added
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-28c6048fcbeb426791dd4be111f873d9
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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