Potassium tert-butoxide → HCID 69009594, compound

HRID 1376102Notes

Reaction equation

HRID 1376102 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[C:20]#[N:21])[C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])[CH3:2].CC(C)([O-])C.[K+]>O1CCCC1>[CH2:1]([O:3][C:4]([C:5]1[N:6]([C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])[C:13]2[C:14]([C:20]=1[NH2:21])=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 85879299HCID 85879299, compound

Product 1

HCID 69009594HCID 69009594, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen, stir and cool to 0° C. a solution [(4-chloro-2-cyanophenyl)-(2,2,2-trifluoro-ethanoyl)amino]-acetic acid ethyl ester (93.34 g, 10 mmol) in tetrahydrofuran (20 mL) and add, dropwise, a 1M solution of potassium tert-butoxide in tetrahydrofuran (12 mL, 12 mmol). Stir the reaction at ambient temperature for 2 h and then partition between aqueous ammonium chloride/ethyl acetate. Separate the organic layer, dry over MgSO4, filter and concentrate to a solid. Triturate the solid with heptane, filter the solid and air dry to obtain 2.86 g (86%) of the title compound: MS 335(M+H), m.p. 249–251° C.

Workup

  1. additionadd
  2. stirringStir
  3. customthe reaction at ambient temperature for 2 h
  4. custompartition between aqueous ammonium chloride/ethyl acetate
  5. customSeparate the organic layer
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate to a solid
  9. customTriturate the solid with heptane
  10. filtrationfilter the solid and air
  11. customdry

Sources & evidence

ORD record
ord-39c304eb5a504e639e12f27fe3927a7e
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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