Tert-butyl 2,2,2-trichloroethanimidate → 6-({5-Chloro-2-[(1,1-dimethylethyl)oxy]phenyl}methyl)-2-pyridine-carboxylic acid

HRID 2356637

反応式

HRID 2356637 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.ClC(Cl)(Cl)C(=N)O[C:23]([CH3:26])([CH3:25])[CH3:24]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

参加物

4

反応物 2

HCID 2734700Tert-butyl 2,2,2-trichloroethanimidateHCID 684564716-[(5-Chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylic acid

生成物 1

HCID 117167306-({5-Chloro-2-[(1,1-dimethylethyl)oxy]phenyl}methyl)-2-pyridine-carboxylic acid収率 24%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution/suspension of 6-[(5-chloro-2-hydroxyphenyl)methyl]-2-pyridine-carboxylic acid (308 mg) in dry dichloromethane (12 ml) was added t-butyl 2,2,2-trichloroacetimidate (1.67 ml) and boron trifluoride-diethyl etherate (0.05 ml) and the mixture stirred under argon at ambient temperature for 44 hours. Dichloromethane (15 ml) was added and the mixture washed with saturated sodium bicarbonate solution (15 ml). The aqueous layer was extracted with dichloromethane (2×15 ml) and the combined organic extracts washed with brine (25 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by mass-directed autopreparation to afford the title compound (91 mg, 24%) as a white solid.

後処理

  1. washthe mixture washed with saturated sodium bicarbonate solution (15 ml)
  2. extractionThe aqueous layer was extracted with dichloromethane (2×15 ml)
  3. washthe combined organic extracts washed with brine (25 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by mass-directed autopreparation

出典と根拠

ORDレコード
ord-f2ccbdd318aa4ffaaf83d4f73eb17e12
出典データセット
uspto-grants-2010_07
特許番号
US07759369B2

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