Lithium hydroxide, monohydrate → {4-[1-(3,5-Dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid

HRID 2363849노트

반응식

HRID 2363849 반응식
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:14]=[C:13]([CH:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)(=[O:23])=[O:22])[CH2:17][CH2:16]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=2)[CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:31][C:26]1[CH:25]=[C:24]([S:21]([N:18]2[CH2:19][CH2:20][CH:15]([C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[C:10]([F:32])[CH:11]=4)[CH:6]=[C:5]([CH2:4][C:3]([OH:33])=[O:2])[CH:14]=3)[CH2:16][CH2:17]2)(=[O:23])=[O:22])[CH:29]=[C:28]([Cl:30])[CH:27]=1

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 86686903HCID 86686903, 화합물

생성물 1

HCID 71604110{4-[1-(3,5-Dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid수율 82%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of {4-[1-(3,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid methyl ester (75 mg, 0.15 mmol) in THF (6 mL) was added a solution of lithium hydroxide monohydrate (30 mg, 0.7 mmol) in water (1.5 mL) and the reaction mixture was stirred for 24 hours at room temperature. The reaction mixture was concentrated under reduced pressure and washed with diethyl ether (3×5 mL). The washings were discarded. Water (5 mL) was added to the residue, and the mixture acidified (pH ˜2-3) with an aqueous solution of hydrochloric acid (2 N) and extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over Na2SO4 and evaporated under reduced pressure to give {4-[1-(3,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid (60 mg, 82%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.35 (br s, 1H), 8.10 (s, 1H), 7.86-8.01 (m, 2H), 7.82 (s, 2H), 7.69 (s, 1H), 7.31-7.44 (m, 2H), 3.85 (d, J=12.2 Hz, 2H), 3.72 (s, 2H), 2.62-2.73 (m, 3H), 1.93 (d, J=12.2 Hz, 2H), 1.69-1.83 (m, 2H); MS cald. for C23H19Cl2FNO4S [(M−H)−]: 494, obsd. 494.2.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashed with diethyl ether (3×5 mL)
  3. additionWater (5 mL) was added to the residue
  4. extractionextracted with ethyl acetate (3×5 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-83af6e9b7ba04f0b8d21ea8213aa739a
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691993B2

반응 노트

불러오는 중…