Sodium Bicarbonate → 4-fluoro-2-((S)-2-methoxy-1-methyl-ethylamino)-benzoic acid tert-butyl ester

HRID 550610Notes

Reaction equation

HRID 550610 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1F)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[CH3:21][O:22][CH2:23][C@@H:24]([NH2:26])[CH3:25]>>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[NH:26][C@@H:24]([CH3:25])[CH2:23][O:22][CH3:21])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 70215362-Propanamine, 1-methoxy-, (2S)-HCID 57447335Tert-butyl 2,4-difluorobenzoate

Product 1

HCID 667373594-fluoro-2-((S)-2-methoxy-1-methyl-ethylamino)-benzoic acid tert-butyl esterYield 84%

Conditions

Temperature
65 °C

Procedure

A mixture of 2,4-difluoro-benzoic acid tert-butyl ester (30 g, 140.05 mmol) and (S)-2-methoxy-1-methyl-ethylamine (100 mL) was stirred at 65° C. for 2 days. A saturated solution of NaHCO3 was added and the mixture was extracted with dichloromethane (3×). The organic phase was washed with water (2×), brine, dried over sodium sulfate filtered and evaporated to dryness to obtain a crude, which was purified by column chromatography on silica gel (exane-EtOAc 9:1). The title compound (33.38 g, 84%) was obtained as oil.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×)
  2. washThe organic phase was washed with water (2×), brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto obtain a crude, which
  7. customwas purified by column chromatography on silica gel (exane-EtOAc 9:1)

Sources & evidence

ORD record
ord-4018fc3a433a476682b6fa34b919530c
Source dataset
uspto-grants-2011_05
Patent number
US07947686B2

Reaction notes

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