HCID 23144410, compound → HCID 23144526, compound

HRID 337523Notes

Reaction equation

HRID 337523 reaction equation
[CH2:1]([O:3][CH2:4][C:5]([C:7]1[S:11][C:10]([N:12](C)[C:13](=O)OC(C)(C)C)=[N:9][C:8]=1[C:21]1[O:22][CH:23]=[CH:24][CH:25]=1)=[O:6])[CH3:2]>FC(F)(F)C(O)=O>[O:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[C:8]1[N:9]=[C:10]([NH:12][CH3:13])[S:11][C:7]=1[C:5]([CH2:4][O:3][CH2:1][CH3:2])=[O:6]

Participants

3

Reactant 1

HCID 23144410HCID 23144410, compound

Product 1

HCID 23144526HCID 23144526, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 623 (550 mg, 1.50 mmol) was dissolved in trifluoroacetic acid (2 mL), followed by stirring for 1 hour. The reaction mixture was concentrated under reduced pressure, and saturated 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 624 (344 mg, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated sodium hydrogencarbonate
  2. additionwas 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-a45c64992c9a45c1a703bf63a17f7d9d
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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