Potassium tert-butoxide → HCID 942254, compound

HRID 1376109Notes

Reaction equation

HRID 1376109 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][C:8]=1[C:17]#[N:18])[CH3:2].CC(C)([O-])C.[K+]>O1CCCC1>[NH2:18][C:17]1[C:8]2[C:7](=[CH:12][C:11]([O:13][CH3:14])=[C:10]([O:15][CH3:16])[CH:9]=2)[NH:6][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:19]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 69010851HCID 69010851, compound

Product 1

HCID 942254HCID 942254, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Stir under N2 a solution of (2-cyano-4,5-dimethoxy-phenylamino)-acetic acid ethyl ester (0.124 g, 0.47 mmol) in tetrahydrofuran (6 mL) and add, dropwise, 1M potassium tert-butoxide in tetrahydrofuran (0.66 mL, 0.66 mmol). Stir for 1 h at ambient temperature and pour into ice/water. Extract with ethyl acetate, dry the extract over MgSO4, filter and concentrate under vacuum to a solid. Chromatograph on a Sep Pak silica gel cartridge (2 g) eluting with dichloromethane and then 2:1 heptane-ethyl acetate. Combine like fractions and concentrate to provide 61.9 mg (49%) of the title compound as a solid: MS 265(M+H).

Workup

  1. additionadd
  2. extractionExtract with ethyl acetate
  3. customdry the
  4. extractionextract over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate under vacuum to a solid
  7. washChromatograph on a Sep Pak silica gel cartridge (2 g) eluting with dichloromethane
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-4f706f3e3b81443e986bd99ed9699ad7
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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