Water → HCID 69200058, compound

HRID 1787320Notes

Reaction equation

HRID 1787320 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH:17]([C:19]1[CH:20]=[C:21]([CH:25]2[C:29]3[C:30]([CH3:44])=[C:31]([NH:36][C:37](=[O:43])[CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C:32]([CH3:35])=[C:33]([CH3:34])[C:28]=3[O:27][CH2:26]2)[CH:22]=[CH:23][CH:24]=1)=O.O>CN(C=O)C>[CH3:40][C:39]([CH3:42])([CH3:41])[CH2:38][C:37]([NH:36][C:31]1[C:32]([CH3:35])=[C:33]([CH3:34])[C:28]2[O:27][CH2:26][CH:25]([C:21]3[CH:20]=[C:19](/[CH:17]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:24]=[CH:23][CH:22]=3)[C:29]=2[C:30]=1[CH3:44])=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 23114314HCID 23114314, compound

Product 1

HCID 69200058HCID 69200058, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of sodium hydride (a 60% dispersion in liquid paraffin, 79 mg, 1.98 mmol) in DMF (10 mL) was added dropwise at 0° C. under an argon atmosphere ethyl diethylphosphonoacetate (444 mg, 1.98 mmol) and the mixture was stirred for 30 minutes. To the reaction solution was added dropwise at 0° C. a solution of N-(3-(3-formylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (684 mg, 1.80 mmol) obtained in Example 173 in DMF (5 mL) and the mixture was stirred for 30 minutes. The reaction solution was warmed to room temperature, was added to water and the product was extracted with ethyl acetate-THF. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to obtain 750 mg (yield: 93%) of the title compound. Melting point: 199-200° C. (ethyl acetate-hexane).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionthe product was extracted with ethyl acetate-THF
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-145810a8102a40548c80632ed0a2a3b5
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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