Water → 2-Amino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester

HRID 906524노트

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HRID 906524 반응식
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[C:7]([C:15]([F:18])([F:17])[F:16])=[CH:6][C:5]=1[NH:19]C(=O)C.O.OS(O)(=O)=O>CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([C:10](=[O:14])[CH2:11][CH2:12][CH3:13])[C:7]([C:15]([F:17])([F:18])[F:16])=[CH:6][C:5]=1[NH2:19]

참가 물질

6

반응물 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 585329572-Acetylamino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester

생성물 1

HCID 119656952-Amino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester수율 82.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

2-Acetylamino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester (234 mg, 0.706 mmol) was dissolved in MeOH (2.4 mL). Water (500 μL) was added, followed by dropwise addition of concd H2SO4 (254 μL). The reaction mixture was heated to 60° C. for 1 h to give a light yellow suspension. The reaction mixture was diluted with EtOAc, poured onto water/EtOAc and the pH was adjusted to 8 with sat. aq KHCO3. The organic phase was washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo. The obtained residue was purified by flash column chromatography (10 g silica gel, hexanes/EtOAc (1:0→7:3)) to afford the title compound (168 mg, 82%) as a colorless foam. ESI-MS: m/z 290 [M+H]+, m/z 288 [M−H]−.

후처리

  1. customto give a light yellow suspension
  2. additionpoured onto water/EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe obtained residue was purified by flash column chromatography (10 g silica gel, hexanes/EtOAc (1:0→7:3))

출처 및 근거

ORD 기록
ord-21b25ca9b4c046b293fe2bb3143081ed
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012988B2

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