Ammonium Acetate → HCID 178502160, compound

HRID 71961Notes

Reaction equation

HRID 71961 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17](=O)[NH:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[N:35]=[C:36]([CH:39]4[CH2:43][CH2:42][CH2:41][N:40]4[C:44](=[O:54])[CH:45]([NH:49][C:50]([O:52][CH3:53])=[O:51])[CH:46]([CH3:48])[CH3:47])[NH:37][CH:38]=3)=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:60]>>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17]1[NH:60][C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]4[N:35]=[C:36]([CH:39]5[CH2:43][CH2:42][CH2:41][N:40]5[C:44](=[O:54])[CH:45]([NH:49][C:50]([O:52][CH3:53])=[O:51])[CH:46]([CH3:47])[CH3:48])[NH:37][CH:38]=4)=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)=[CH:19][N:18]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 178502171HCID 178502171, compound

Product 1

HCID 178502160HCID 178502160, compoundYield 98.6%

Conditions

Temperature
135 °C

Procedure

1-[2-(4′-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-1H-imidazol-4-yl}-biphenyl-4-yl)-2-oxo-ethylcarbamoyl]-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (147.8 mg) was taken into m-xylenes (2.0 mL) and heated at 135° C. Solid ammonium acetate (120 mg, 1.5 mmol) was added and the reaction was stirred at 135° C. After 180 minutes, the reaction was cooled to room temperature and the volatiles were removed in vacuo. The crude reaction product was partitioned between EtOAc and water. The organic layer was collected and dried over sodium sulfate. Filtration and evaporation of solvents gave the crude product (142 mg).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customthe volatiles were removed in vacuo
  3. customThe crude reaction product
  4. customwas partitioned between EtOAc and water
  5. customThe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and evaporation of solvents

Sources & evidence

ORD record
ord-1b0dbccce57d4ffd9fcf0f570f3db646
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

Loading…