Water → HCID 69200058, compound

HRID 2376520Notes

Reaction equation

HRID 2376520 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-6a427e02781a48b081898cec4c9d8266
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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