Cesium carbonate → HCID 9956126, compound

HRID 1609983Notes

Reaction equation

HRID 1609983 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([SH:13])=[CH:9][C:8]=1[CH2:14][CH2:15][CH3:16])C.Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[O:23][C:24]=1[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:25][C:24]1[O:23][C:22]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=2)=[N:21][C:20]=1[CH2:19][S:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:3])=[O:17])=[C:8]([CH2:14][CH2:15][CH3:16])[CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazoleHCID 207681114-Mercapto-2-propylphenoxy-acetic acid ethyl ester

Product 1

HCID 9956126HCID 9956126, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of (4-mercapto-2-propyl-phenoxy)-acetic acid ethyl ester (127 mg, 0.5 mmol) and 4-Chloromethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (131 mg, 0.48 mmol) in acetonitrile (2 mL) was added cesium carbonate (326 mg, 1 mmol). After 4 h at room temperature, the reaction was quenched by water, extracted with ethyl acetate. Combined organic layers were washed with brine, dried (sodium sulfate) and concentrated. The residue was taken into THF (2 mL) and treated with lithium hydroxide (1N, 0.5 mL) at room temperature for 2 h. THF was evaporated, the residue was treated with water (0.5 mL) and extracted with ether. The aqueous was acidified with 5 N HCl, extracted with ether, dried over sodium sulfate and concentrated. The crude product was purified by reversed phase HPLC to give the title compound (125 mg, 53.7%)

Workup

  1. customthe reaction was quenched by water
  2. extractionextracted with ethyl acetate
  3. washCombined organic layers were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. additiontreated with lithium hydroxide (1N, 0.5 mL) at room temperature for 2 h
  7. customTHF was evaporated
  8. additionthe residue was treated with water (0.5 mL)
  9. extractionextracted with ether
  10. extractionextracted with ether
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated
  13. customThe crude product was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-50406eb7e06e47f2bec567ac384d7370
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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