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

HRID 1894028ノート

反応式

HRID 1894028 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

2-Acetylamino-5-butyryl-4-trifluoromethyl-benzoic acid methyl ester (234 mg, 0.706 mmol) was dissolved in MeOH (2.4 mL). Water (500 uL) was added, followed by dropwise addition of concd H2SO4 (254 uL). 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]−.

後処理

  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))

出典と根拠

ORDレコード
ord-a73b59bb63b043c28eb8742a9e0e9e1a
出典データセット
uspto-grants-2013_08
特許番号
US08513268B2

反応ノート

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