Ethyl Acetate → HCID 178450822、化合物

HRID 2169234ノート

反応式

HRID 2169234 の反応式
[C:1]1([C:7]2[C:8]([CH2:13][C:14]([NH2:16])=[NH:15])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([O:21][C:22](=[O:37])/[C:23](/O)=[C:24](\[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[C:25](O)=[O:26])([CH3:20])([CH3:19])[CH3:18].C[O-].[Na+].C(OCC)(=O)C>CO.CCCCCC>[C:17]([O:21][C:22]([C:23]1[C:24]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:25]([OH:26])[N:16]=[C:14]([CH2:13][C:8]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[N:15]=1)=[O:37])([CH3:20])([CH3:18])[CH3:19]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 867258802-(3-Phenyl-pyridin-2-yl)-acetamidineHCID 86725882(E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester

生成物 1

HCID 178450822HCID 178450822、化合物収率 48.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8058Hexane溶媒

実験手順

To a stirred solution of 2-(3-phenyl-pyridin-2-yl)-acetamidine (162) (300 mg, 1.10 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester (4) (511 mg, 1.66 mmol) in methanol (5 mL) was added sodium methoxide (1.3 mL, 3.32 mmol) at 0° C., then the reaction mixture was allowed to warm to room temperature, stirred for 16 h. Silica thin layer chromatography was performed (50% ethyl acetate in hexane, Rf=0.3). After completion of the reaction, it was quenched with water, methanol was evaporated and water (30 mL) was added. The mixture was extracted with ethyl acetate (3×30 mL) and the separated organic part was dried and concentrated to get a crude product, which was purified by a CombiFlash column (eluted at 90% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(3-phenyl-pyridin-2-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (163) (250 mg, 48.1%) as a yellow sticky product.

後処理

  1. customAfter completion of the reaction, it
  2. customwas quenched with water, methanol
  3. customwas evaporated
  4. additionwater (30 mL) was added
  5. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
  6. customthe separated organic part was dried
  7. concentrationconcentrated
  8. customto get a crude product, which
  9. customwas purified by a CombiFlash column (eluted at 90% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-1d328b6d972445f8a104422304cd2968
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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