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

HRID 1468417
ノート
印刷プレビュー

反応式

HRID 1468417 の反応式
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]([Cl:33])[CH:14]=2)[CH:9]=1.C1COCC1.O>CCCCCC>[Cl:33][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH2:7][C:6]([OH:34])=[O:5])[C:17]([CH3:18])=[C:16]2[C:19]1[CH:24]=[CH:23][C:22]([S:25](=[O:31])(=[O:32])[N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 86695008[6-Chloro-4-(4-diethylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

生成物 1

HCID 71711381[6-Chloro-4-(4-diethylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid収率 95%

試薬・触媒・溶媒 1

HCID 8058Hexane
溶媒

実験手順

Lithium hydroxide monohydrate (0.015 g, 0.34 mmol) was added to a stirred solution of [6-chloro-4-(4-diethylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (0.040 g, 0.09 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 gave [6-chloro-4-(4-diethylsulfamoyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid (0.037 g, 95%) as a solid. 1H NMR (DMSO-d6) δ: 12.49 (br. s, 1H), 7.98 (d, J=8.3 Hz, 3H), 7.91 (s, 1H), 7.49 (d, J=8.3 Hz, 3H), 7.00 (s, 1H), 3.86 (s, 2H), 3.28 (s, 4H), 2.07 (s, 3H), 1.08 (t, J=7.1 Hz, 6H). MS calcd. for C23H25ClNO4S [(M+H)+] 446, obsd. 446.4.

後処理

  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

出典と根拠

ORDレコード
ord-c96beebb079c47289fc1b69185ed77f6
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09000044B2

反応ノート

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