Potassium Carbonate → HCID 10237397, compound

HRID 2211681Notes

Reaction equation

HRID 2211681 reaction equation
[O:1]=[S:2]1(=[O:32])[C:7](C(=O)C(F)(F)F)=[CH:6][N:5]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][C:15]=2[F:31])[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+]>CO.C([O-])(O)=O.[Na+]>[O:32]=[S:2]1(=[O:1])[CH:3]=[CH:4][N:5]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][C:15]=2[F:31])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59997904HCID 59997904, compound

Product 1

HCID 10237397HCID 10237397, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The product of Step 2 (0.670 g, 1.39 mmol) is suspended in 28 mL of methanol, and the solution heated to reflux. Dry K2CO3 (0.386 g, 2.8 mmol) is added, and the mixture is stirred at reflux for 1 h. Upon cooling, the solution is diluted with 2.5% aq. NaHCO3 (20 mL) and the methanol removed by rotary evaporation. The resulting aqueous phase is extracted with EtOAc (5×30 mL), and the combined organic layers are dried (MgSO4). Solvent is evaporated under vacuum, and the crude material purified by silica gel column chromatography (gradient 0–4% MeOH-DCM) to afford the title compound as a white solid. Yiled 0.309 g (58%). Rf=0.13 (5% MeOH-DCM). M.p. 193°–194° C.

Workup

  1. temperaturethe solution heated to reflux
  2. temperatureat reflux for 1 h
  3. temperatureUpon cooling
  4. customthe methanol removed by rotary evaporation
  5. extractionThe resulting aqueous phase is extracted with EtOAc (5×30 mL)
  6. dry with materialthe combined organic layers are dried (MgSO4)
  7. customSolvent is evaporated under vacuum
  8. customthe crude material purified by silica gel column chromatography (gradient 0–4% MeOH-DCM)

Sources & evidence

ORD record
ord-8778d36a58db49628cafe8157ffb3ade
Source dataset
uspto-grants-2006_09
Patent number
US07101874B2

Reaction notes

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