HCID 23144557, compound → HCID 86060929, compound

HRID 1967772Notes

Reaction equation

HRID 1967772 reaction equation
[C:1]([C:9]1[S:13][C:12]([NH:14]C(=O)OC(C)(C)C)=[N:11][C:10]=1[C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[C:2]1([C:1]([C:9]2[S:13][C:12]([NH2:14])=[N:11][C:10]=2[C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)=[O:8])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 23144557HCID 23144557, compound

Product 1

HCID 86060929HCID 86060929, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 135 (6.18 g, 16.7 mmol) was dissolved in trifluoroacetic acid (17 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate were added to the 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 136 (4.39 g, 97%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additiona saturated aqueous solution of sodium hydrogencarbonate were added to the 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-9b50566b1f3b4500bc8aa16a1d5c73c2
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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