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

HRID 1921097
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HRID 1921097 반응식
[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]
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참가 물질

4

반응물 3

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

생성물 1

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

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온도
65 °C

실험 절차

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 satured 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-06f9a82032de4564ad5aeae19e33ee04
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173659B2

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