Potassium Carbonate → HCID 76684541, compound

HRID 925228Notes

Reaction equation

HRID 925228 reaction equation
[CH2:1]([CH:3]1[C:11]2[C:10]3[CH2:12][CH2:13][N:14](C(=O)C(F)(F)F)[CH2:15][CH2:16][C:9]=3[CH:8]=[CH:7][C:6]=2[O:5][CH2:4]1)[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO.O>[CH2:1]([CH:3]1[C:11]2[C:10]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16][C:9]=3[CH:8]=[CH:7][C:6]=2[O:5][CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86725337HCID 86725337, compound

Product 1

HCID 76684541HCID 76684541, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The product of step (i) (45 mg, 0.143 mmol) was dissolved in an appropriately sized flask in MeOH (3 ml). To this mixture water (1 ml) and K2CO3 (500 mg, 3.62 mmol) were added. The reaction mixture was stirred at room temperature until the product formation was complete by LCMS. The reaction mixture was diluted with water (>10× total volume) and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to provide the title compound (15.8 mg). 1H NMR (300 MHz, CDCl3) δ 6.86 (d, J=7.8 Hz, 1H); 6.52 (d, J=8.1 Hz, 1H); 4.49-4.44 (m, 1H); 4.39-4.35 (m, 1H); 3.31-3.21 (m, 1H); 2.99-2.85 (m, 8H); 2.07 (bs, 1H); 1.58-1.52 (m, 2H); 0.92 (t, J=7.5 Hz, 3H). MS: ESI (positive): 218 (M+H).

Workup

  1. extractionextracted with DCM (3×)
  2. washThe combined DCM extracts were washed with brine
  3. dry with materialdried (Na2SO4), and solvent
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-3e0a0b3ee90b407d8368bb547be635b5
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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