Hydrochloric Acid → HCID 178457437、化合物

HRID 2169295ノート

反応式

HRID 2169295 の反応式
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.Cl>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:42]([CH3:44])[CH3:43])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 178457474HCID 178457474、化合物

生成物 1

HCID 178457437HCID 178457437、化合物収率 75.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (257) (0.7 g, 1.13 mmol) in tetrahydrofuran (10.0 mL) was added HCl (0.062 g, 1.70 mmol) and the reaction mixture was stirred at room temperature for 1.5 h. After completion of the reaction, the mixture was extracted with ethyl acetate. The combined organic layer was washed with water, separated and dried over Na2SO4. After evaporation of the solvent, the crude product was purified by normal silica gel column chromatography (using 60% ethyl acetate in hexane followed by 5% methanol in ethyl acetate) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-isopropylamide (258) (0.43 g, 75.0%) as a white solid.

後処理

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water
  4. customseparated
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by normal silica gel column chromatography (using 60% ethyl acetate in hexane followed by 5% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-c09dd0da38c04b5f831538f7a2d99d62
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

読み込み中…