Ethyl Acetate → HCID 178524880、化合物

HRID 2169409ノート

反応式

HRID 2169409 の反応式
C([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])[N:9]=1)=[O:7])(C)(C)C.O[Li].O.C(OCC)(=O)C>O1CCCC1.O.CCCCCC>[CH2:15]([O:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][C:10]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Br:31])=[N:11][C:12]=1[OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178450820HCID 178450820、化合物

生成物 1

HCID 178524880HCID 178524880、化合物収率 94.7%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (376) (14 g, 27.723 mmol) in tetrahydrofuran-water (15:7, 220 mL) was added LiOH.H2O (11.644 g, 277.228 mmol). The reaction mixture was refluxed for 16 h while silica thin layer chromatography was performed (50% ethyl acetate in hexane; Rf=0.1). After completion of the reaction, all volatiles were removed and the residue was diluted with water (50 mL) and neutralized to pH 7 with 1N HCl. The mixture was filtered and the resulting solid was dried to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid (377) (11.8 g, 94.65%) as a white solid.

後処理

  1. temperatureThe reaction mixture was refluxed for 16 h while silica thin layer chromatography
  2. customAfter completion of the reaction
  3. customall volatiles were removed
  4. additionthe residue was diluted with water (50 mL)
  5. filtrationThe mixture was filtered
  6. customthe resulting solid was dried

出典と根拠

ORDレコード
ord-56e78e9572824edbace6c0818f3c002e
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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