Perchloric Acid → Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate

HRID 590970Notes

Reaction equation

HRID 590970 reaction equation
Cl(O)(=O)(=O)=O.[OH:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9]>C(OC(C)(C)C)(=O)C>[C:17]([O:6][CH:7]([C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:15][CH:16]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:22])([CH3:18])[CH3:14]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 70818588Methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate

Product 1

HCID 70818322Methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetateYield 83.8%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

Under a nitrogen atmosphere, perchloric acid (70%, 4 mL) was added at −10° C. to a solution of methyl 2-hydroxy-2-(2-phenyl-1,3-thiazol-4-yl)acetate (6a) (800 mg, 3.2 mmol) in terbutyl acetate (25 mL). After 1 hour, the reaction was quenched with a saturated solution of sodium bicarbonate (20 mL) and extracted with dichloromethane (2×20 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 80/20) to afford the desired product (6b) as a white pale oil (410 mg, 1.34 mmol, 42%).

Workup

  1. customthe reaction was quenched with a saturated solution of sodium bicarbonate (20 mL)
  2. extractionextracted with dichloromethane (2×20 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 80/20)

Sources & evidence

ORD record
ord-9fcc35f547584d4ca6793579ec4017a8
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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