Potassium Carbonate → HCID 67404569, compound

HRID 350570Notes

Reaction equation

HRID 350570 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) δ 1.17 (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-29b8d8d32f9d4328b5aba27042823191
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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