Hydrochloric Acid → HCID 18447135, compound

Temperature

60 °C

A 6N aqueous hydrochloric acid solution (0.355 ml, 2.13 mmol) was added dropwise to a solution of N-[3-methoxy-4-(methoxymethoxy)-2-methylphenyl]-2,2-dimethylpropanamide (300 mg, 1.07 mmol) in methanol (3 ml) at room temperature. After 18 hours, the reaction solution was poured into water (30 ml) and extracted with ethyl acetate (30 ml×2), and the ethyl acetate layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The ethyl acetate layer dried was concentrated under reduced pressure, and to a solution of the resulting residue in pyridine (3 ml) was added methanesulfonyl chloride (0.091 ml, 1.17 mmol) at 0° C. The resulting mixture was heated to 60° C. After 2.5 hours, the reaction solution was concentrated under reduced pressure and the resulting residue was poured into water (50 ml) and extracted with ethyl acetate (30 ml×2). The extract solution was dried over anhydrous magnesium sulfate. The extract solution dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-[(2,2-dimethylpropanoyl)amino]-2-methoxy-3-methylphenyl methanesulfonate (338 mg, 100%).

1. extractionextracted with ethyl acetate (30 ml×2)
2. washthe ethyl acetate layer was washed with a saturated aqueous sodium chloride solution
3. dry with materialdried over anhydrous magnesium sulfate
4. dry with materialThe ethyl acetate layer dried
5. concentrationwas concentrated under reduced pressure
6. waitAfter 2.5 hours
7. concentrationthe reaction solution was concentrated under reduced pressure
8. additionthe resulting residue was poured into water (50 ml)
9. extractionextracted with ethyl acetate (30 ml×2)
10. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
11. customThe extract solution dried
12. concentrationwas concentrated under reduced pressure
13. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

ORD record

ord-b3bf7ae639f04c378401ada0a10a96d5

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2