Formaldehyde → Ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylate

HRID 1789807Notes

Reaction equation

HRID 1789807 reaction equation
C(NCC)C.O.[CH2:7]([O:9][C:10](=[O:30])[CH:11]([CH2:15][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)[C:12](O)=O)[CH3:8].C=O>C(Cl)Cl>[CH2:7]([O:9][C:10](=[O:30])[C:11]([CH2:15][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)=[CH2:12])[CH3:8]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8021DiethylamineHCID 537177962-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid monoethyl ester

Product 1

HCID 54494317Ethyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)acrylateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylamine (0.29 g, 3.00 mmol), water (2 mL) and methylene chloride (2 mL) was added to a mixture of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.00 g, 2.96 mmol) and 37% aq. solution of formaldehyde (0.25 g, 3.05 mmol) at 0° C. The mixture was stirred for 16 h at room temperature and then poured onto ice-water and extracted with methylene chloride. The organic layer was washed with 5% NaHCO3 and dried. Filtration and concentration under reduced pressure gave 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.75 g, 83%).

Workup

  1. additionpoured onto ice-water
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with 5% NaHCO3
  4. customdried
  5. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-2f8a6931a93f483288158d8ee6690ca6
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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