HCID 23144648, compound → HCID 23144251, compound

HRID 1967781Notes

Reaction equation

HRID 1967781 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:19]C(=O)OC(C)(C)C)[S:9][C:10]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[O:12]>FC(F)(F)C(O)=O>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]([C:10]1[S:9][C:8]([NH2:19])=[N:7][C:6]=1[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:12]

Participants

3

Reactant 1

HCID 23144648HCID 23144648, compound

Product 1

HCID 23144251HCID 23144251, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 185 (286 mg, 0.770 mmol) was dissolved in trifluoroacetic acid (2 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 186 (208 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-7ad475bb96ec41cab89bf3845c8b1ca6
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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