tert-Butyl acetate → HCID 70819501, compound

HRID 591042Notes

Reaction equation

HRID 591042 reaction equation
[OH:1][CH:2]([C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[CH:15]=1)[C:3]([O:5][CH3:6])=[O:4].Cl(O)(=O)(=O)=O.C(=O)([O-])O.[Na+].C(O[C:30]([CH3:33])([CH3:32])[CH3:31])(=O)C>>[C:30]([O:1][CH:2]([C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[CH:15]=1)[C:3]([O:5][CH3:6])=[O:4])([CH3:33])([CH3:32])[CH3:31]

Participants

5

Reactant 4

HCID 10908tert-Butyl acetateHCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 70818317HCID 70818317, compound

Product 1

HCID 70819501HCID 70819501, compoundYield 55%

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-hydroxy-2-{imidazo[1,2-a]pyridin-2-yl}acetate (25b) (153 mg, 0.74 mmol) in tert-butyl acetate (12 mL) at 0° C. was added perchloric acid (1.5 mL). The mixture was stirred at 0° C. for 15 minutes and at room temperature for 45 minutes before being poured into a saturated aqueous solution of sodium hydrogencarbonate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 50/50) to provide the desired product (25c) (108 mg, 0.41 mmol, 55%) as a colorless oil.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 50/50)

Sources & evidence

ORD record
ord-c844e58058494f9e9d895d521ba4cb47
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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