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

HRID 1789798

반응식

HRID 1789798 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-d548d65a3035443ebaa3c97adc92d402
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071175B1

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