Sulfuric Acid → 2-Amino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 1441555노트

반응식

HRID 1441555 반응식
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19]C(=O)C.OS(O)(=O)=O>CO.O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[C:7]([C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]=1[NH2:19]

참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 585329182-Acetylamino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester

생성물 1

HCID 119654552-Amino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester수율 70.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

A solution of 2-acetylamino-5-(tetrahydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester (8.25 g, 24.9 mmol) in MeOH (100 mL) and water (10 mL) was cooled to 0° C. Concd H2SO4 (6.88 mL, 125 mmol) was added dropwise. The solution was refluxed for 45 min, cooled to r.t., diluted with ice/water and extracted with EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 1:4 EtOAc/hexanes) to give the title product (5.06 g, 68%) as colorless crystals. m.p.: 131-136° C., API-ES: m/z 290 [M+H]+.

후처리

  1. temperatureThe solution was refluxed for 45 min
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel, 1:4 EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-7e43a64c90ac4f09b399380b1e505c12
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655666B2

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