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

HRID 1789913Notes

Reaction equation

HRID 1789913 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-af4686a75b474273b708218cdf042d3f
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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