Lithium hydroxide, monohydrate → {6-Fluoro-3-methyl-4-[4-(4-trifluoromethoxy-phenyl-sulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid

HRID 1468428노트

반응식

HRID 1468428 반응식
O.[OH-].[Li+].C[O:5][C:6](=[O:41])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:39])(=[O:38])[NH:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:40])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[F:40][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:41])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:24]=[CH:23][C:22]([S:25](=[O:39])(=[O:38])[NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:35])[F:36])=[CH:29][CH:28]=2)=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695015{6-Fluoro-3-methyl-4-[4-(4-trifluoromethoxy-phenylsulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

생성물 1

HCID 71711444{6-Fluoro-3-methyl-4-[4-(4-trifluoromethoxy-phenyl-sulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid수율 84%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

Lithium hydroxide monohydrate (0.012 g, 0.39 mmol) was added to a stirred solution of {6-fluoro-3-methyl-4-[4-(4-trifluoromethoxy-phenylsulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (0.038 g, 0.07 mmol) in a 3:1 mixture of THF—H2O mixture (5 mL). The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was concentrated to remove THF, and the crude material was diluted with water, acidified [pH˜2] with a 6 N aqueous solution of hydrochloric acid. The mixture was extracted twice with ethyl acetate. The collected organic layers were washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. Trituration with hexane afforded {6-fluoro-3-methyl-4-[4-(4-trifluoromethoxy-phenyl-sulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid (0.031 g, 84%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.46 (br. s, 1 H), 10.56 (br. s, 1 H), 7.99 (dd, J=9.00, 6.40 Hz, 1 H), 7.90 (m, J=8.30 Hz, 2 H), 7.88 (s, 1 H), 7.42 (m, J=8.30 Hz, 2 H), 7.37 (td, J=8.80, 2.40 Hz, 1 H), 7.21-7.31 (m, 4 H), 6.49 (dd, J=11.00, 2.60 Hz, 1 H), 3.82 (s, 2 H), 1.99 (s, 3 H). MS calcd. for C26H18F4NO5S [(M−H)−] 532, obsd. 532.0.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customto remove THF
  3. additionthe crude material was diluted with water
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washThe collected organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product

출처 및 근거

ORD 기록
ord-d5ea3d9902314590b0a9a1b4d63f2741
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000044B2

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