Ethyl Acetate → 2-Amino-5-(1-ethoxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 906511ノート

反応式

HRID 906511 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([OH:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17]C(=O)C.O.[C:23]1(C)C=CC(S(O)(=O)=O)=C[CH:24]=1.CCOC(C)=O>CCO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([O:12][CH2:23][CH3:24])[CH3:11])[C:7]([C:13]([F:14])([F:15])[F:16])=[CH:6][C:5]=1[NH2:17]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 591644842-Acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester

生成物 1

HCID 119653762-Amino-5-(1-ethoxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester収率 179%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester (500 mg, 1.64 mmol) in EtOH (5 mL) was treated with p-toluenesulfonic acid monohydrate (100 mg, 0.518 mmol) and stirred at r.t. for 5 d. The reaction mixture was taken into EtOAc and washed with sat. aq NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 5:1 hexanes/EtOAc) to give title product (270 mg, 57%) as colorless crystals. m.p.: 100-103° C., API-ES: m/z 292 [M+H]+.

後処理

  1. washwashed with sat. aq NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 5:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-8b245073ad484ec0815a1023645a7d1a
出典データセット
uspto-grants-2011_09
特許番号
US08012988B2

反応ノート

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