Ammonium Acetate → HCID 67383470, compound

HRID 335885Notes

Reaction equation

HRID 335885 reaction equation
C([O-])(=O)C.[NH4+].[F:6][C:7]([F:39])([CH2:11][C:12]1(O)[C:25]2[CH:24]=[C:23]([O:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=[CH:21][C:20]=2[O:19][C:18]2[C:13]1=[CH:14][C:15]([C:32]1[CH:33]=[N:34][CH:35]=[N:36][CH:37]=1)=[CH:16][CH:17]=2)[C:8]([NH2:10])=[O:9]>CC(O)C.O.C(=O)(O)[O-].[Na+]>[F:6][C:7]1([F:39])[C:8](=[O:9])[NH:10][C:12]2([C:25]3[CH:24]=[C:23]([O:26][CH2:27][C:28]([CH3:30])([CH3:31])[CH3:29])[CH:22]=[CH:21][C:20]=3[O:19][C:18]3[C:13]2=[CH:14][C:15]([C:32]2[CH:37]=[N:36][CH:35]=[N:34][CH:33]=2)=[CH:16][CH:17]=3)[CH2:11]1

Participants

6

Reactant 2

HCID 517165Ammonium AcetateHCID 67382945HCID 67382945, compound

Product 1

HCID 67383470HCID 67383470, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
90 °C

Procedure

Ammonium acetate (0.131 g, 1.704 mmol) was added to a solution of 2,2-difluoro-3-(9-hydroxy-2-(neopentyloxy)-7-(pyrimidin-5-yl)-9H-xanthen-9-yl)propanamide (0.04 g, 0.085 mmol) in 2-Propanol (0.852 mL) and the reaction was heated to 90° C. After 30 minutes the reaction was diluted with water and saturated aqueous sodium bicarbonate (50 mL) and extracted with CH2Cl2 (3×25 mL). The combined organic extracts were washed with water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to afford a residue that was purified by silica gel chromatography (1:1 EtOAc in hexane) to provide 4,4-difluoro-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)spiro[pyrrolidine-2,9′-xanthen]-5-one. M=452.1 [M+H].

Workup

  1. extractionextracted with CH2Cl2 (3×25 mL)
  2. washThe combined organic extracts were washed with water, saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customto afford a residue that
  7. customwas purified by silica gel chromatography (1:1 EtOAc in hexane)

Sources & evidence

ORD record
ord-a6837086566f48e3ad4a9d1fccb9cb29
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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