Methyl iodide → HCID 86587806, compound

HRID 350569Notes

Reaction equation

HRID 350569 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([NH:5][C@@H:6]([CH3:19])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=[O:4].[C:22]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[CH3:22][N:5]([C@@H:6]([CH3:19])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)[C:3](=[O:4])[C:2]([F:20])([F:21])[F:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86587804HCID 86587804, compound

Product 1

HCID 86587806HCID 86587806, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl (S)-4-[2-(trifluoroacetamido)-1-propoxy]benzoate (695 mg, 2.28 mmol) and K2CO3 (630 mg, 4.56 mmol) in DMF (10 ml) was added MeI (210 ml, 3.37 mmol) and the reaction mixture was stirred at room temperature for 2 days. The mixture was diluted with H2O and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with EtOAc-CHCl3 (1:19, v/v) as eluent to give methyl (S)-4-[2-[(N-methyl)trifluoroacetamido]-1-propoxy]benzoate (720 mg, 99%) as a white solid. mp 73–75° C.; 1H-NMR (CDCl3) δ 1.36–1.39 (m, 3 H), 2.96 and 3.10 (each s, total 3 H), 3.89 (s, 3 H), 3.99–4.14 (m, 2 H), 4.84–4.92 (m, 1 H), 6.88–6.92 (m, 2 H), 7398–8.00 (m, 2 H); MS (FAB) m/z 320 (M++1); Anal. Calcd for C14H16F3NO4: C, 52.67; H, 5.05; F, 17.85; N, 4.39. Found: C, 52.76; H, 5.09; F, 17.53; N, 4.32.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica-gel with EtOAc-CHCl3 (1:19

Sources & evidence

ORD record
ord-9bb6409b2ef74f0da326341371cfa614
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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