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

HRID 1789854Notes

Reaction equation

HRID 1789854 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-e8dccdb06f9e44fabf50426169d54b15
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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