Citric Acid → 4-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid

HRID 914361ノート

反応式

HRID 914361 の反応式
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([CH2:20][CH2:21][C:22]2[N:23]=[C:24]([S:27][C:28]([CH3:36])([CH3:35])[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30])[S:25][CH:26]=2)[C:12]2[N:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][N:13]=2)=[CH:6][CH:5]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[C:31]([C:29](=[O:30])[C:28]([S:27][C:24]1[S:25][CH:26]=[C:22]([CH2:21][CH2:20][N:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=2)[C:12]2[N:13]=[CH:14][C:15]([CH2:18][CH3:19])=[CH:16][N:17]=2)[N:23]=1)([CH3:35])[CH3:36])([CH3:32])([CH3:33])[CH3:34]

参加物

6

反応物 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 673973504-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester

生成物 1

HCID 673979184-{[(2-{2-[(2-Tert-butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid収率 93.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

4-{[(2-{2-[(2-tert-Butyl-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}ethyl)(5-ethylpyrimidin-2-yl)amino]methyl}benzoic acid methyl ester (2.2 g) synthesized in Example 437-1 was dissolved in methanol (50 mL) and tetrahydrofuran (50 mL), 1N aqueous sodium hydroxide solution (16 ml) was added, and the mixture was stirred at 60° C. for 4 hr. Aqueous 10% citric acid solution was added, and the mixture was extracted with chloroform. The insoluble material was filtered off, and the filtrate was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (2.0 g) as an oil.

後処理

  1. extractionthe mixture was extracted with chloroform
  2. filtrationThe insoluble material was filtered off
  3. washthe filtrate was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-b2741d158073431cb141bd49fed25898
出典データセット
uspto-grants-2011_09
特許番号
US08026370B2

反応ノート

読み込み中…