Formaldehyde → HCID 54443463, compound

HRID 1789888Notes

Reaction equation

HRID 1789888 reaction equation
C(NCC)C.[CH2:6]([O:8][C:9](=[O:31])[CH:10]([CH2:14][C:15]1[CH:16]=[N:17][C:18]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:19]([CH:21]=[CH2:22])[CH:20]=1)[C:11](O)=O)[CH3:7].C=O>C(Cl)Cl>[CH2:6]([O:8][C:9](=[O:31])[C:10]([CH2:14][C:15]1[CH:16]=[N:17][C:18]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:19]([CH:21]=[CH2:22])[CH:20]=1)=[CH2:11])[CH3:7]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 54417312HCID 54417312, compound

Product 1

HCID 54443463HCID 54443463, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylamine (0.85 ml, 8.80 mmol) was added dropwise to a mixture of 2-(6-tert-butoxycarbonylamino-5-vinyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (3.05 g, 8.37 mmol) and 37% aq. solution of formaldehyde (0.71 g, 8.80 mmol) in CH2Cl2 (2 ml) at 0° C. The mixture was stirred for 3 h at room temperature and then poured onto ice-water and extracted with dichloromethane. The organic layer was washed with 5% NaHCO3 and dried. Flash chromatography (1% methanol in CH2Cl2) yielded 2-(6-tert-butoxycarbonylamino-5-vinyl-pyridin-3-ylmethyl)- acrylic acid ethyl ester (1.70 g, 61%).

Workup

  1. additionpoured onto ice-water
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with 5% NaHCO3
  4. customdried

Sources & evidence

ORD record
ord-7b84ac93008f48beb153b198eb691b10
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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