HCID 23144288, compound → HCID 86612471, compound

HRID 337516Notes

Reaction equation

HRID 337516 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([CH3:19])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[O:12]>FC(F)(F)C(O)=O>[CH3:19][C:13]1([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])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

3

Reactant 1

HCID 23144288HCID 23144288, compound

Product 1

HCID 86612471HCID 86612471, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 582 (210 mg, 0.535 mmol) was dissolved in trifluoroacetic acid (2 mL), followed by stirring at room temperature for 1 hour. The solvent was distilled away under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the resulting residue, followed by extraction with ethyl acetate. 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 (ethyl acetate) to afford the entitled Compound 583 (156 mg, 100%).

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the resulting residue
  3. extractionfollowed by extraction with ethyl acetate
  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 (ethyl acetate)

Sources & evidence

ORD record
ord-15b92126ff92499baf40dc9937606dbb
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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