Lithium Hydroxide → 1-(Cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylic acid

HRID 1844708ノート

反応式

HRID 1844708 の反応式
[CH:1]1([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([S:14](=[O:20])(=[O:19])[NH:15][CH:16]3[CH2:18][CH2:17]3)[CH:10]=[C:9]2[C:21]([O:23]CC)=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-]>CO.O>[CH:1]1([CH2:7][N:8]2[C:12]([CH3:13])=[C:11]([S:14](=[O:20])(=[O:19])[NH:15][CH:16]3[CH2:17][CH2:18]3)[CH:10]=[C:9]2[C:21]([OH:23])=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 70869105Ethyl 1-(cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 708691941-(Cyclohexylmethyl)-4-(N-cyclopropylsulfamoyl)-5-methyl-1H-pyrrole-2-carboxylic acid収率 80.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To a solution of compound 3a (8.0 g, 22.0 mmol) in MeOH (200 mL) was added a solution of LiOH (4.2 g, 100 mmol) in water (50 mL) and the solution was warmed to 50° C. overnight, cooled to rt and concentrated. The residue was diluted with water and acidified to pH˜4 with 4N aq. HCl and the solution was extracted with EA twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=2/1) to give compound 3b (6.0 g, 80%) as a white solid.

後処理

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. additionThe residue was diluted with water
  4. extractionthe solution was extracted with EA twice
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by CC (PE/EA=2/1)

出典と根拠

ORDレコード
ord-e71df508eb1f48b590385f378e248ca5
出典データセット
uspto-grants-2015_02
特許番号
US08946446B2

反応ノート

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