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

HRID 1526059Notes

Reaction equation

HRID 1526059 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 times). The organic phase was washed twice with water then with brine, dried over sodium sulfate filtered and evaporated to dryness to obtain a crude, which was purified by column chromatography on silica gel (exane/ethyl acetate 9:1). The title compound (33.38 g, 84%) was obtained as oil.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3 times)
  2. washThe organic phase was washed twice with water
  3. dry with materialwith brine, dried 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/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-94ed94bdd65a4673a73f4c092c5e9fbc
Source dataset
uspto-grants-2015_07
Patent number
US09085558B2

Reaction notes

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