Ammonia → HCID 19348435, compound

HRID 1637446Notes

Reaction equation

HRID 1637446 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:33])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][C:24]=1[O:31][CH3:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH3:4])([CH3:3])[CH3:2].[NH3:34].C(OCC)(=O)C>C(#N)C.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:12])[NH2:34])=[CH:7][C:6]=1[NH:14][C:15](=[O:33])[CH2:16][CH:17]([C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:30])=[CH:25][C:24]=1[O:31][CH3:32])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 19348865HCID 19348865, compound

Product 1

HCID 19348435HCID 19348435, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

510 mg (3.15 mmol) of N,N'-carbonyldiimidazole were added to a solution of 1.142 g (2.42 mmol) of N-(2-t-butyl-5-carboxyphenyl)-3-(2-methoxy-4-methylthiophenyl)octanamide (prepared as described in Preparation 31A) in 10 ml of acetonitrile, and the resulting mixture was stirred at room temperature for 1 hour, after which 0.79 ml (12.1 mmol) of 28% w/w aqueous ammonia. The reaction mixture was stirred for 5 hours, after which it was diluted with water, and the diluted aqueous mixture was freed from the organic solvent by distillation under reduced pressure. The aqueous concentrate was extracted with ethyl acetate. The extract was washed with 2 N aqueous hydrochloric acid, with a 0.5 N aqueous solution of sodium hydroxide, with water and with a saturated aqueous solution of sodium chloride, after which it was dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was recrystallized from ethyl acetate, to give 962 mg (yield 84%) of the title compound as crystals, melting at 171-172° C. (from ethyl acetate).

Workup

  1. stirringThe reaction mixture was stirred for 5 hours
  2. distillationthe diluted aqueous mixture was freed from the organic solvent by distillation under reduced pressure
  3. concentrationThe aqueous concentrate
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with 2 N aqueous hydrochloric acid, with a 0.5 N aqueous solution of sodium hydroxide, with water and with a saturated aqueous solution of sodium chloride
  6. dry with materialafter which it was dried over magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-0f09417044444e42814b280e123a8ae8
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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