Formaldehyde → 2-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-acrylic acid ethyl ester

HRID 1789854ノート

反応式

HRID 1789854 の反応式
C(NCC)C.[CH2:6]([O:8][C:9](=[O:30])[CH:10]([CH:14]([C:16]1[CH:17]=[N:18][C:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:20][CH:21]=1)[CH3:15])[C:11](O)=O)[CH3:7].C=O.CCOC(C)=O>C(Cl)Cl>[CH2:6]([O:8][C:9](=[O:30])[C:10]([CH:14]([C:16]1[CH:17]=[N:18][C:19]([NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])=[CH:20][CH:21]=1)[CH3:15])=[CH2:11])[CH3:7]

参加物

6

反応物 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 696503142-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid monoethyl ester

生成物 1

HCID 696502442-[1-(6-Tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-acrylic acid ethyl ester収率 41.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Diethylamine (0.153 mL, 1.473 mmol) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid monoethyl ester (423 mg, 1.2 mmol) and formaldehyde (132 mg, 1.626 mmol, 36% in water) in methylene chloride (2 mL) at 0° C. under argon. The mixture was stirred at room temperature over night. EtOAc was added and the solution was washed with water, NaHCO3 and brine, dried and concentrated under reduced pressure. Flash chromatography (toluene/EtOAc, 3:1) gave 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-acrylic acid ethyl ester (158 mg, 41%).

後処理

  1. washthe solution was washed with water, NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e8dccdb06f9e44fabf50426169d54b15
出典データセット
uspto-grants-2006_07
特許番号
US07071175B1

反応ノート

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