Sodium Bicarbonate → HCID 59442955, compound

HRID 1959113Notes

Reaction equation

HRID 1959113 reaction equation
[F:1][C:2]1[C:7]2[C:8]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[C:4]([NH:21]C(=O)OC(C)(C)C)[CH:3]=1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[F:1][C:2]1[C:7]2[C:8]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[C:4]([NH2:21])[CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59443007HCID 59443007, compound

Product 1

HCID 59442955HCID 59442955, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the compound obtained in (8) described above (148 mg) in trifluoroacetic acid (2 mL) was stirred at room temperature for an hour. The reaction solution was added dropwise to a saturated aqueous solution of sodium bicarbonate, and the mixture was extracted with chloroform. The organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=80/20 to 40/60) to give the titled compound (94 mg) as a pale yellow powder.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=80/20 to 40/60)

Sources & evidence

ORD record
ord-fdf0da63361045fc8b7f8ca9179184ef
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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