Perchloric Acid → HCID 70855540, compound

HRID 591003Notes

Reaction equation

HRID 591003 reaction equation
Cl(O)(=O)(=O)=O.[O:6]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[N:17]=[C:18]([CH3:28])[S:19][C:20]=3[CH:21]([OH:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7]1>C(OC(C)(C)C)(=O)C>[C:10]([O:27][CH:21]([C:20]1[S:19][C:18]([CH3:28])=[N:17][C:16]=1[C:14]1[CH:13]=[CH:12][C:11]2[O:6][CH2:7][CH2:8][CH2:9][C:10]=2[CH:15]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])([CH3:15])([CH3:11])[CH3:9]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 70855539HCID 70855539, compound

Product 1

HCID 70855540HCID 70855540, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

Under a nitrogen atmosphere, perchloric acid (70%, 700 μL) was added at −10° C. to a solution of ethyl 2-[4-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-methyl-1,3-thiazol-5-yl]-2-hydroxyacetate (13b) (90 mg, 0.27 mmol) in terbutyl acetate (5 mL). After 1 hour, the reaction was quenched with a saturated aqueous solution of sodium bicarbonate (10 mL) and extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 70/30) to afford the desired product (13c) as a white solid (50 mg, 0.13 mmol, 48%).

Workup

  1. customthe reaction was quenched with a saturated aqueous solution of sodium bicarbonate (10 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 70/30)

Sources & evidence

ORD record
ord-e726ca487a2a48479da05efb2448737a
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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