Potassium Carbonate → HCID 67404569, compound

HRID 354510Notes

Reaction equation

HRID 354510 reaction equation
[CH3:1][N:2]([C@@H:9]([CH3:22])[CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)C(=O)C(F)(F)F.C([O-])([O-])=O.[K+].[K+]>CO.O.O>[CH3:1][NH:2][C@@H:9]([CH3:22])[CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86587806HCID 86587806, compound

Product 1

HCID 67404569HCID 67404569, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred solution of methyl (S)-4-[2-[(N-methyl)trifluoroacetamido]-1-propoxy]benzoate (710 mg, 2.22 mmol) in MeOH—H2O (10 ml, 1:1, v/v) was added K2CO3 (460 mg, 3.33 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with H2O and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated to give methyl (S)-4-[2-(N-methylamino)-1-propoxy]benzoate (430 mg, 87%) as a colorless oil. 1H-NMR (CDCl3) δ1.17 (d, J=6.6 Hz, 3 H), 2.48 (s, 3 H), 2.98-3.06 (m, 1 H), 3.86-3.96 (series of s and m, total 5 H), 6.92 (d, J=9.0 Hz, 2 H), 7.98 (d, J=9.0 Hz, 2 H).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-2d2c4abea7be4f0c8a5b938d55baafbd
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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