Methacrylic Acid → HCID 66795860, compound

HRID 535226Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:12]([OH:17])(=[O:16])[C:13]([CH3:15])=[CH2:14].Cl[CH2:19][C:20]([N:22]1[C:28](=[O:29])[CH:27]2[CH:23]1[CH2:24][CH2:25][CH2:26]2)=[O:21]>[I-].[K+].O.C(OCC)(=O)C>[C:12]([O:17][CH2:19][C:20]([N:22]1[C:28](=[O:29])[CH:27]2[CH:23]1[CH2:24][CH2:25][CH2:26]2)=[O:21])(=[O:16])[C:13]([CH3:15])=[CH2:14]

Participants

Conditions

Temperature: 25 °C

Procedure

In a four-necked flask with a volume of 500 mL, which was equipped with a thermometer, a stirrer, a dropping funnel, and a nitrogen introducing tube, 9.7 g (70 mmol) of potassium carbonate, 0.7 g (4 mmol) of potassium iodide, 100 mL of dimethylformamide, 25.8 g (300 mmol) of methacrylic acid, and 18.8 g (100 mmol) of 6-chloroacetyl-6-azabicyclo[3.2.0]heptan-7-one obtained in Synthesis Example 3 were charged, and the mixture was stirred at an internal temperature of 25° C. for 5 hours. To the reaction mixture, 100 mL of ethyl acetate and 50 mL of water were added, and a liquid separation operation was then carried out. The obtained organic layer was concentrated under reduced pressure and then purified by means of silica gel column chromatography, thereby obtaining 17.1 g (72 mmol) of 6-methacryloyloxyacetyl-6-azabicyclo[3.2.0]heptan-7-one having the following properties.

Workup

customobtained in Synthesis Example 3
additionwere charged
customa liquid separation operation
concentrationThe obtained organic layer was concentrated under reduced pressure
custompurified by means of silica gel column chromatography

Sources & evidence

ORD record: ord-fcb535d3566648bf9274f9c27f81d923
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859183B2

Reaction notes

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