Ethanol → Ethyl 5-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-(4-methoxybenzyloxymethyl)-1H-pyrrol-3-carboxylate

HRID 2097531Notes

Reaction equation

HRID 2097531 reaction equation
C(O)C.[CH:4]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:19](=O)[CH2:20][CH:21]([C:27](=O)[CH2:28][O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:12]=[CH:13][C:14]=2[O:15][CH:16]([F:18])[F:17])[CH2:6][CH2:5]1.C([O-])(=O)C.[NH4+:45]>O>[CH:4]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:19]3[NH:45][C:27]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=4)=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:20]=3)[CH:12]=[CH:13][C:14]=2[O:15][CH:16]([F:18])[F:17])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 517165Ammonium AcetateHCID 66602693Ethyl 2-[2-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-oxoethyl]-4-(4-methoxybenzyloxy)-3-oxobutyrate

Product 1

HCID 66602560Ethyl 5-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-(4-methoxybenzyloxymethyl)-1H-pyrrol-3-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 100 ml of ethanol solution containing 14.0 g (26.8 mmol) of ethyl 2-[2-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-2-oxoethyl]-4-(4-methoxybenzyloxy)-3-oxobutyrate obtained in Reference example 45-(b) was added 10.3 g (134 mmol) of ammonium acetate, the mixture was stirred at room temperature for 1 hour, and further stirred at 80° C. for 4 hours. After completion of the reaction, to the reaction mixture were added water and a saturated aqueous solution of sodium chloride, and the mixture was extracted with chloroform. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=7:3 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 10.3 g of the title compound as a beige solid. (Yield: 77%)

Workup

  1. stirringfurther stirred at 80° C. for 4 hours
  2. customAfter completion of the reaction
  3. extractiona saturated aqueous solution of sodium chloride, and the mixture was extracted with chloroform
  4. customThe organic layer after separation
  5. washwas washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. additionthe fractions containing the desired compound
  9. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-ceb77f283b7a4f5da678512e84e1c7f6
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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