Lithium Hydroxide → 4-[N-Methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pent-2-enoic acid

HRID 583416ノート

反応式

HRID 583416 の反応式
C([O:3][C:4](=[O:37])[CH:5]=[CH:6][CH:7]([N:19]([CH3:36])[C:20](=[O:35])[C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)[CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)C.[OH-].[Li+]>CO.O1CCCC1.O>[CH3:36][N:19]([CH:7]([CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH:6]=[CH:5][C:4]([OH:37])=[O:3])[C:20](=[O:35])[C:21]1[CH:22]=[C:23]([C:31]([F:33])([F:34])[F:32])[CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1

参加物

6

反応物 2

HCID 3939Lithium HydroxideHCID 571817134-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pent-2-enoic acid ethyl ester

生成物 1

HCID 538480544-[N-Methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pent-2-enoic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 23.0 g of 4-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pent-2-enoic acid ethyl ester [see example 20d)] and 9.23 g of lithium hydroxide (monohydrate) in 240 ml of methanol, 175 ml of tetrahydrofuran and 72 ml of water is stirred at room temperature for 120 minutes and then concentrated by evaporation. The residue is dissolved in 200 ml of water, acidified to pH=2 with 0.1N hydrochloric acid and extracted three times using 200 ml of ethyl acetate each time. The combined organic phases are washed with water and saturated NaCl solution, dried (magnesium sulfate) and concentrated by evaporation. Filtration of the residue over silica gel with hexane/ethyl acetate 1:1 yields the title compound in the form of a yellow foam. Rf value=0.41 (methylene chloride/methanol 19:1). IR(CH2Cl2) cm-1 : 3050,1709, 1644, 1402, 1337,1277, 1183,1142, 905, 849, 821

後処理

  1. concentrationconcentrated by evaporation
  2. dissolutionThe residue is dissolved in 200 ml of water
  3. extractionextracted three times
  4. washThe combined organic phases are washed with water and saturated NaCl solution
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated by evaporation
  7. filtrationFiltration of the residue over silica gel with hexane/ethyl acetate 1:1

出典と根拠

ORDレコード
ord-2f55b58763ed4f6daf69bd590d5e7541
出典データセット
uspto-grants-1999_07
特許番号
US05929067

反応ノート

読み込み中…