Formaldehyde → 2-(2-Tert-butoxycarbonylamino-pyridin-4-ylmethyl)-acrylic acid ethyl ester

HRID 1789798

反応式

HRID 1789798 の反応式
C(NCC)C.[CH2:6]([O:8][C:9](=[O:29])[CH:10]([CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]=1)[C:11](O)=O)[CH3:7].C=O>C(Cl)Cl>[CH2:6]([O:8][C:9](=[O:29])[C:10]([CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]=1)=[CH2:11])[CH3:7]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 545486422-(2-Tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid monoethyl ester

生成物 1

HCID 544852162-(2-Tert-butoxycarbonylamino-pyridin-4-ylmethyl)-acrylic acid ethyl ester収率 71.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of diethylamine (0.26 g, 2.67 mmol) in methylene chloride (4 mL) was added to a mixture of 2-(2-tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid monoethyl ester (0.90 g, 2.66 mmol) and 37% aq. solution of formaldehyde (0.24 g, 3.00 mmol) at 0° C. The mixture was stirred for 5 h at room temperature and the mixture was poured onto ice-water and extracted with methylene chloride. The organic layer was washed with 5% NaHCO3 and dried. The crude product was purified by flash chromatography (1% methanol in CH2Cl2) to yield 2-(2-tert-butoxycarbonylamino-pyridin4-ylmethyl)-acrylic acid ethyl ester (0.58 g, 71%).

後処理

  1. additionthe mixture was poured onto ice-water
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with 5% NaHCO3
  4. customdried
  5. customThe crude product was purified by flash chromatography (1% methanol in CH2Cl2)

出典と根拠

ORDレコード
ord-d548d65a3035443ebaa3c97adc92d402
出典データセット
uspto-grants-2006_07
特許番号
US07071175B1

関連ノート

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