Formaldehyde → 2-(6-Tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester

HRID 1789862Notes

Reaction equation

HRID 1789862 reaction equation
C(NCC)C.[CH2:6]([O:8][C:9](=[O:30])[CH:10]([CH2:14][C:15]1[C:16]([CH3:29])=[N:17][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:19][CH:20]=1)[C:11](O)=O)[CH3:7].C=O>C(Cl)Cl>[CH2:6]([O:8][C:9](=[O:30])[C:10]([CH2:14][C:15]1[C:16]([CH3:29])=[N:17][C:18]([NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[CH:19][CH:20]=1)=[CH2:11])[CH3:7]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 54453537HCID 54453537, compound

Product 1

HCID 544728422-(6-Tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diethylamine (359 mg, 4.90 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.44 g, 4.09 mmol) and formaldehyde (464 mg, 5.72 mmol, 37% in water) in methylene chloride (35 mL) at 0° C. under argon. The mixture was stirred at room temperature over night. Methylene chloride was added and the solution was washed with Na2CO3 and brine, dried and concentrated under reduced pressure to give 2-(6-tert-butoxycarbonylamino-2-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (1.03 g, 79%).

Workup

  1. washthe solution was washed with Na2CO3 and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25f326f9f0f54f25b93e2ee1d2fd505f
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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