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

HRID 1789913노트

반응식

HRID 1789913 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-af4686a75b474273b708218cdf042d3f
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071175B1

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