Ammonia → N-(2-t-Butyl-5-carbamoylphenyl)-3-[4-(1-oxobutyl)-2-methoxyphenyl]octanamide

HRID 1637451Notes

Reaction equation

HRID 1637451 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](O)=[O:12])=[CH:7][C:6]=1[NH:14][C:15](=[O:36])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:33])[CH2:30][CH2:31][CH3:32])=[CH:25][C:24]=1[O:34][CH3:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH3:4])([CH3:3])[CH3:2].[NH3:37].CCCCCC.C(OCC)(=O)C>C(#N)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:12])[NH2:37])=[CH:7][C:6]=1[NH:14][C:15](=[O:36])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([C:29](=[O:33])[CH2:30][CH2:31][CH3:32])=[CH:25][C:24]=1[O:34][CH3:35])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8058HexaneHCID 8857Ethyl AcetateHCID 19348698N-(2-t-butyl-5-carboxyphenyl)-3-(4-butyryl-2-methoxyphenyl)octanamide

Product 1

HCID 19348622N-(2-t-Butyl-5-carbamoylphenyl)-3-[4-(1-oxobutyl)-2-methoxyphenyl]octanamideYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

210 mg (1.30 mmol) of N,N'-carbonyldiimidazole were added to a suspension of 530 mg (1.07 mmol) of N-(2-t-butyl-5-carboxyphenyl)-3-(4-butyryl-2-methoxyphenyl)octanamide (prepared as described in Preparation 64C), in 10 ml of acetonitrile, and the resulting mixture was stirred for 35 minutes, after which 1.0 ml (15 mmol) of concentrated aqueous ammonia were added. The reaction mixture was stirred for 20 minutes, after which it was freed from the organic solvent by distillation under reduced pressure. The concentrate was extracted with ethyl acetate. The extract was washed with 2 N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 50 g of silica gel using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 1:9 to 0:9 by volume as the eluent, to give 511 mg (yield 97%) of the title compound as a foam-like substance.

Workup

  1. stirringThe reaction mixture was stirred for 20 minutes
  2. distillationafter which it was freed from the organic solvent by distillation under reduced pressure
  3. extractionThe concentrate was extracted with ethyl acetate
  4. washThe extract was washed with 2 N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through 50 g of silica gel using
  8. washa gradient elution method

Sources & evidence

ORD record
ord-a0955cd9722242408904fba0d29dd448
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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