HCID 23144649, compound → HCID 23144445, compound

HRID 1361817Notes

Reaction equation

HRID 1361817 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:20]C(=O)OC(C)(C)C)[S:9][C:10]=1[C:11]([C:13]1[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:12]>FC(F)(F)C(O)=O>[CH3:19][C:14]1[C:13]([C:11]([C:10]2[S:9][C:8]([NH2:20])=[N:7][C:6]=2[C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:12])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

3

Reactant 1

HCID 23144649HCID 23144649, compound

Product 1

HCID 23144445HCID 23144445, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 308 (83.0 mg, 0.215 mmol) was dissolved in trifluoroacetic acid (1 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate were added to the resulting residue, and the organic layer was separated. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:4) to afford the entitled Compound 309 (60.0 mg, 99%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additiona saturated aqueous solution of sodium hydrogencarbonate were added to the resulting residue
  3. customthe organic layer was separated
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-b12bf49916a745279c5e463b057b2667
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

Loading…