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

HRID 2356637

반응식

HRID 2356637 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f2ccbdd318aa4ffaaf83d4f73eb17e12
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759369B2

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