Formaldehyde → HCID 54506217, compound

HRID 1789883Notes

Reaction equation

HRID 1789883 reaction equation
C(NCC)C.O.[CH2:7]([O:9][C:10](=[O:31])[CH:11]([CH2:15][C:16]1[CH:17]=[N:18][C:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:20]([Cl:22])[CH:21]=1)[C:12](O)=O)[CH3:8].C=O>C(Cl)Cl>[CH2:7]([O:9][C:10](=[O:31])[C:11]([CH2:15][C:16]1[CH:17]=[N:18][C:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:20]([Cl:22])[CH:21]=1)=[CH2:12])[CH3:8]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 8021DiethylamineHCID 53805939HCID 53805939, compound

Product 1

HCID 54506217HCID 54506217, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diethylamine (3.67 ml, 3.67 mmol) was added dropwise followed by water (2.5 ml) and CH2Cl2 (2.5 ml) to a mixture of 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.40 g, 3.64 mmol) and 37% aq. solution of formaldehyde (0.29 ml, 3.75 mmol) in CH2Cl2 (2 ml) at 0° C. The mixture was stirred for 20 h at room temperature and then poured onto ice-water and extracted with methylene chloride. The organic layer was washed with 5% NaHCO3, dried and concentrated under reduced pressure. Flash chromatography (1-2.5% methanol in CH2Cl2) yielded 2-(6-tert-butoxycarbonylamino-5-chloro-pyridin-3-ylmethyl)-acrylic acid ethyl ester 0.81 g (65%).

Workup

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

Sources & evidence

ORD record
ord-e2c9e2935db24053a2e1db4febb08675
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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