Potassium Carbonate → HCID 71143565, compound

HRID 571454Notes

Reaction equation

HRID 571454 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Cl.[NH:14]1[CH2:17][CH:16]([OH:18])[CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[OH:18][CH:16]1[CH2:17][N:14]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:15]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 27592903-Hydroxyazetidine hydrochloride

Product 1

HCID 71143565HCID 71143565, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of ethyl 4-fluorobenzoate (0.841 g, 5.00 mmol, Aldrich: Cat. #102644), azetidin-3-ol hydrochloride (0.438 g, 4.00 mmol, Aldrich: Cat. #680079) and potassium carbonate (1.38 g, 9.98 mmol) in dimethyl sulfoxide (4 mL) was heated at 180° C. for 2 hours. After cooling, the mixture was diluted with ethyl acetate (50 mL), and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-50%) to afford the desired product (0.643 g, 72.6%). LCMS (M+H)+: m/z=222.1.

Workup

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-50%)

Sources & evidence

ORD record
ord-892fb1ae497f4c87bd6f2987f86614f7
Source dataset
uspto-grants-2015_05
Patent number
US09023840B2

Reaction notes

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