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Lithium hydroxide, monohydrate → [4-(4-Diethylsulfamoyl-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid

HRID 1468435
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HRID 1468435 반응식
O.[OH-].[Li+].C[O:5][C:6](=[O:34])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:32])(=[O:31])[N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:33])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[CH2:29]([N:26]([CH2:27][CH3:28])[S:25]([C:22]1[CH:23]=[CH:24][C:19]([C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:33])[CH:14]=3)[CH:9]=[C:8]([CH2:7][C:6]([OH:34])=[O:5])[C:17]=2[CH3:18])=[CH:20][CH:21]=1)(=[O:31])=[O:32])[CH3:30]
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참가 물질

5

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HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695020[4-(4-Diethylsulfamoyl-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

생성물 1

HCID 71711511[4-(4-Diethylsulfamoyl-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid수율 88.9%

시약·촉매·용매 1

HCID 8058Hexane
용매

실험 절차

Lithium hydroxide monohydrate (0.020 g, 0.45 mmol) was added to a stirred solution of [4-(4-diethylsulfamoyl-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (0.05 g, 0.11 mmol) in a 3:1 mixture of THF—H2O mixture (6 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 gave [4-(4-diethylsulfamoyl-phenyl)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid (0.042 g, 87%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.48 (br. s, 1 H), 8.01 (dd, J=9.20, 6.20 Hz, 1 H), 7.97 (d, J=8.31 Hz, 2 H), 7.91 (s, 1 H), 7.48 (d, J=8.31 Hz, 2 H), 7.39 (td, J=8.80, 2.40 Hz, 1 H), 6.68 (dd, J=11.00, 2.40 Hz, 1 H), 3.85 (s, 2 H), 3.28 (q, J=7.10 Hz, 4 H), 2.07 (s, 3 H), 1.09 (t, J=7.09 Hz, 6 H). MS calcd. for C23H23FNO4S [(M−H)−] 428, obsd. 428.0.

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-9d2a79cdc5f5464a9cd2862381ec551c
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000044B2

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