Methyl diethylphosphonoacetate → HCID 68831233, compound

HRID 987599Notes

Reaction equation

HRID 987599 reaction equation
C(OP([CH2:9][C:10]([O:12][CH3:13])=[O:11])(OCC)=O)C.[CH3:14][Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:24]1([C:30]2([CH2:37][NH:38][C:39]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[O:47][CH3:48])=[O:40])[CH2:35][CH2:34]C(=O)[CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH3:13][O:12][C:10]([CH:9]1[CH2:34][CH2:35][C:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([CH2:37][NH:38][C:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[O:47][C:48]#[CH:14])=[O:40])[CH2:31][CH2:32]1)=[O:11]

Participants

5

Reactant 3

HCID 66113Methyl diethylphosphonoacetateHCID 2733832Lithium HexamethyldisilazideHCID 102687052-methoxy-N-[(4-oxo-1-phenylcyclohexyl)methyl]benzamide

Product 1

HCID 68831233HCID 68831233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl diethylphosphonoacetate (0.088 mL, 0.48 mmol) in 2 mL of THF was added lithium bis(trimethylsilyl)amide (0.48 mL, 1N, 0.48 mmol in THF) at 0° C. and the reaction mixture stirred for 50 min The solution was then added to a solution of 4-phenyl-4-(3-(2-methoxyphenyl)-3-oxo-2-azaprop-1-yl)cyclohexanone (67.1 mg, 0.20 mmol) in 2 mL of THF at −78° C. and the solution was allowed to warm to rt overnight. The solution was then filtered through a plug of silica gel, concentrated and was purified by flash chromatography (silica, EtOAc/Hexane, 3:7) to give the title compound.

Workup

  1. filtrationThe solution was then filtered through a plug of silica gel
  2. concentrationconcentrated
  3. customwas purified by flash chromatography (silica, EtOAc/Hexane, 3:7)

Sources & evidence

ORD record
ord-9724479296d847c0b5207bc2f064ddb9
Source dataset
uspto-grants-2003_10
Patent number
US06632836B1

Reaction notes

Loading…