Ammonium Acetate → HCID 178502142, compound

HRID 79901Notes

Reaction equation

HRID 79901 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13](=O)[NH:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[C:29]([C:34]4[N:35]=[C:36]([CH:39]5[CH2:45][C:42]6([CH2:44][CH2:43]6)[CH2:41][N:40]5[C:46](=[O:56])[CH:47]([NH:51][C:52]([O:54][CH3:55])=[O:53])[CH:48]([CH3:50])[CH3:49])[NH:37][CH:38]=4)[CH:30]=3)[CH:25]=2)=[CH:20][CH:19]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:62]>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13]1[NH:62][C:16]([C:18]2[CH:19]=[CH:20][C:21]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[C:29]([C:34]5[N:35]=[C:36]([CH:39]6[CH2:45][C:42]7([CH2:43][CH2:44]7)[CH2:41][N:40]6[C:46](=[O:56])[CH:47]([NH:51][C:52]([O:54][CH3:55])=[O:53])[CH:48]([CH3:50])[CH3:49])[NH:37][CH:38]=5)[CH:30]=4)[CH:25]=3)=[CH:22][CH:23]=2)=[CH:15][N:14]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 178502143HCID 178502143, compound

Product 1

HCID 178502142HCID 178502142, compoundYield 44.3%

Conditions

Temperature
135 °C

Procedure

2-{2-[4-(6-{2-[5-(2-Methoxycarbonylamino-3-methyl-butyryl)-5-aza-spiro[2.4]hept-6-yl]-1H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-2-oxo-ethylcarbamoyl}-thiazolidine-3-carboxylic acid tert-butyl ester (350 mg, 0.44 mmol) was dissolved in m-xylenes (3.0 mL) and heated at 135° C. Solid ammonium acetate (400 mg, 9.07 mmol) was added and the reaction was stirred at 135° C. After 45 minutes, the reaction was cooled to room temperature and the volatiles were removed in vacuo. The crude reaction product was partitioned between chloroform and water. The organic layer was collected and dried over sodium sulfate. Filtration and evaporation of solvents gave the crude product. The crude material was purified via silica gel chromatography (eluent: EtOAc/hexanes) to yield the product (151.3 mg, 0.195 mmol).

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 chloroform and water
  5. customThe organic layer was collected
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and evaporation of solvents
  8. customgave the crude product
  9. customThe crude material was purified via silica gel chromatography (eluent: EtOAc/hexanes)

Sources & evidence

ORD record
ord-e14dda5f1b6b4f5d95b1a669a5cb8497
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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