Ethyl Acetate → HCID 178457452、化合物

HRID 2169411ノート

反応式

HRID 2169411 の反応式
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[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[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Br:37])[N:15]=1)=[O:13])(C(C)(C)C)(C)C.C(OCC)(=O)C>O1CCCC1.Cl.CCCCCC>[OH:8][CH2:9][CH2:10][N:11]([CH:38]([CH3:40])[CH3:39])[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Br:37])[N:15]=1)=[O:13]

参加物

6

反応物 2

HCID 8857Ethyl AcetateHCID 178457486HCID 178457486、化合物

生成物 1

HCID 178457452HCID 178457452、化合物収率 85.45%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (378) (5.7 g, 8.80 mmol) in tetrahydrofuran (50 mL), 1N HCl (15 mL) was added and the reaction mixture was stirred for 1 h at room temperature while silica thin layer chromatography was performed (70% ethyl acetate in hexane; Rf=0.2). After completion of the reaction, volatiles were removed and the residue was diluted with water (30 mL) and adjusted to pH 8 using NaHCO3. The aqueous mixture was extracted with ethyl acetate (2×150 mL) and the combined extracts were dried and concentrated. The resulting residue was purified by column over normal silica gel (100-200) to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylicacid(2-hydroxyethyl)-isopropylamide (379) (4.02 g, 85.45%) as a white solid.

後処理

  1. customAfter completion of the reaction, volatiles
  2. customwere removed
  3. additionthe residue was diluted with water (30 mL)
  4. extractionThe aqueous mixture was extracted with ethyl acetate (2×150 mL)
  5. customthe combined extracts were dried
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column over normal silica gel (100-200)

出典と根拠

ORDレコード
ord-446fdd30242542928f4fca99cb289326
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…