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

Lithium hydroxide monohydrate (0.009 g, 0.21 mmol) was added to a stirred solution of {6-chloro-3-methyl-4-[4-(4-trifluoromethoxy-phenylsulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (0.030 g, 0.05 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-chloro-3-methyl-4-[4-(4-trifluoromethoxy-phenyl-sulfamoyl)-phenyl]-naphthalen-2-yl}-acetic acid (0.02 g, 69%) as a solid. 1H NMR (DMSO-d6) δ: 12.49 (br. s, 1H), 10.56 (br. s, 1H), 7.82-8.03 (m, 4H), 7.38-7.54 (m, 3H), 7.27-7.35 (m, 2H), 7.19-7.27 (m, 2H), 6.82 (s, 1H), 3.84 (s, 2H), 1.99 (s, 3H). MS calcd. for C26H18ClF3NO5S [(M−H)−] 548, obsd. 548.0.

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

ORD 기록

ord-b3954115493f4a818d238b1e28dd62d7

출처 데이터셋

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09000044B2