Trifluoroacetic acid → 5-Cyclohex-1-enyl-3-aminothiophene-2-carboxylic acid methyl ester

HRID 2099696ノート

反応式

HRID 2099696 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]2(O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:8][C:9]=1[NH:10]C(OC(C)(C)C)=O)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)=[CH:8][C:9]=1[NH2:10])=[O:4]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 577953883-tert-Butoxycarbonylamino-5-(1-hydroxy-cyclohexyl)-thiophene-2-carboxylic acid methyl ester

生成物 1

HCID 577954015-Cyclohex-1-enyl-3-aminothiophene-2-carboxylic acid methyl ester収率 76.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-tert-butoxycarbonylamino-5-(1-hydroxy-cyclohexyl)-thiophene-2-carboxylic acid methyl ester (68 g, 0.192 mol) in 400 mL of dichloromethane at 0° C. (ice bath) was added trifluoroacetic acid (400 mL). The mixture was stirred for 30 min at 0° C. and followed by TLC. After completion, the reaction mixture was evaporated to dryness and partitioned between ethyl acetate and saturated water solution of NaHCO3. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was triturated in 4.4 volume of hexane for 30 min. Then filtered and washed with cold hexane. Dried in the vacuum oven to afford 35 g (76%) of 3-Amino-5-cyclohex-1-enyl-thiophene-2-carboxylic acid methyl ester.

後処理

  1. customAfter completion, the reaction mixture was evaporated to dryness
  2. custompartitioned between ethyl acetate and saturated water solution of NaHCO3
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was triturated in 4.4 volume of hexane for 30 min
  7. filtrationThen filtered
  8. washwashed with cold hexane
  9. customDried in the vacuum oven

出典と根拠

ORDレコード
ord-b44d46609452451eb55dca3e656e1f93
出典データセット
uspto-grants-2009_08
特許番号
US07569600B2

反応ノート

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