HCID 23144787, compound → HCID 86060931, compound

HRID 1361834Notes

Reaction equation

HRID 1361834 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17]C(=O)OC(C)(C)C)[S:9][C:10]=1[C:11]([CH2:13][CH2:14][O:15][CH3:16])=[O:12]>FC(F)(F)C(O)=O>[CH3:16][O:15][CH2:14][CH2:13][C:11]([C:10]1[S:9][C:8]([NH2:17])=[N:7][C:6]=1[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:12]

Participants

3

Reactant 1

HCID 23144787HCID 23144787, compound

Product 1

HCID 86060931HCID 86060931, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 409 (124 mg, 0.343 mmol) was dissolved in trifluoroacetic acid (3 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium hydrogencarbonate was added to the 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 410 (79.0 mg, 87%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the 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-59d68fedec6141cba0c7bcaac64ad765
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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