Formaldehyde → 2-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl ester

HRID 1789913ノート

反応式

HRID 1789913 の反応式
C(NCC)C.[CH2:6]([O:8][C:9](=[O:35])[CH:10]([CH:14]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11](O)=O)[CH3:7].C=O>C(Cl)Cl.C(OCC)(=O)C>[CH2:6]([O:8][C:9](=[O:35])[C:10]([CH:14]([C:21]1[CH:22]=[N:23][C:24]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH2:11])[CH3:7]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 543127722-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid monoethyl ester

生成物 1

HCID 537546282-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl ester収率 23%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Diethylamine (0.52 mL, 5.04 mmol) was added to a mixture of 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid monoethyl ester (1.7 g, 4.1 mmol) and 37% aq. solution of formaldehyde (0.42 mL, 5.6 mmol) in methylene chloride (6.5 mL) at 0° C. The mixture was stirred overnight at room temperature and then diluted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate and is brine and dried. After filtration and evaporation in vacuo the crude product was purified by flash chromatography (CH2Cl2) to yield 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-acrylic acid ethyl ester (0.36 g, 23%).

後処理

  1. washThe organic layer was washed with aqueous saturated sodium bicarbonate
  2. customdried
  3. filtrationAfter filtration and evaporation in vacuo the crude product
  4. customwas purified by flash chromatography (CH2Cl2)

出典と根拠

ORDレコード
ord-af4686a75b474273b708218cdf042d3f
出典データセット
uspto-grants-2006_07
特許番号
US07071175B1

反応ノート

読み込み中…