Potassium Carbonate → HCID 86656375, compound

HRID 1942560Notes

Reaction equation

HRID 1942560 reaction equation
[CH:1]([N:4]([C:18]([C:20]1[C:21]([C:43]([F:46])([F:45])[F:44])=[CH:22][C:23]2[O:28][C:27]([CH3:34])([CH2:29][O:30]C#CC)[C:26](=[O:35])[N:25]([CH2:36][CH2:37][NH:38][C:39]#[C:40][CH3:41])[C:24]=2[CH:42]=1)=[O:19])[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CO>[OH:30][CH2:29][C:27]1([CH3:34])[C:26](=[O:35])[N:25]([CH2:36][CH2:37][NH:38][C:39]#[C:40][CH3:41])[C:24]2[CH:42]=[C:20]([C:18]([N:4]([CH:1]([CH3:2])[CH3:3])[C@@H:5]3[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]3)=[O:19])[C:21]([C:43]([F:46])([F:44])[F:45])=[CH:22][C:23]=2[O:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 86656374HCID 86656374, compound

Product 1

HCID 86656375HCID 86656375, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (3R)-3-(isopropyl{[2-methyl-3-oxo-4-[2-(propynylamino)ethyl]-2-[(propynyl-oxy)methyl]-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}amino)piperidine-1-carboxylate (24.9 g) was dissolved in methanol (100 mL), and thereto was added potassium carbonate (553 mg), and the mixture was stirred at 0° C. for one hour. After the reaction was complete, a saturated aqueous ammonium chloride solution was added thereto, and methanol was removed by evaporation under reduced pressure. The residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by column chromatography to give the title compound (4.92 g).

Workup

  1. custommethanol was removed by evaporation under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-af531ba5ad5a46e4a3670b4ccaf59ca0
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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