Ammonia → HCID 53715601, compound

HRID 1418161Notes

Reaction equation

HRID 1418161 reaction equation
C(N1C=CN=C1)(N1[CH:7]=[CH:6]N=C1)=O.[C:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:25])=O)=[CH:19][C:18]=1[NH:26][C:27](=[O:45])[CH2:28][CH:29]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]2[O:41][CH2:42][CH2:43][O:44][C:36]=12)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(C)(C)[CH3:14].[NH3:46]>C(#N)C>[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[NH2:46])=[CH:19][C:18]=1[NH:26][C:27](=[O:45])[CH2:28][CH:29]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]2[O:41][CH2:42][CH2:43][O:44][C:36]=12)[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:14][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 19348784HCID 19348784, compound

Product 1

HCID 53715601HCID 53715601, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

165 mg (1.02 mmol) of 1,1'-carbonylbis(1H-imidazole) were added to a solution of 355 mg (0.783 mmol) of N-(2-t-butyl-5-carboxyphenyl)-3-(2,3-ethylenedioxyphenyl)octanamide (prepared as described in Preparation 74C) in 7.0 ml of dry acetonitrile, and the resulting mixture was stirred at room temperature for 30 minutes, after which 0.46 ml of 29% v/v aqueous ammonia was added. The reaction mixture was stirred at room temperature for 1 hour, after which the mixture was freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel using ethyl acetate as the eluent, to give 327 mg (yield 92%) of the title compound as a colorless foam-like substance.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  2. distillationafter which the mixture was freed from the solvent by distillation under reduced pressure
  3. customThe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-54bdbfd9adb5408e9614267f12e5a312
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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