1,2-Dichloroethane → HCID 178520009, compound

tert-Butyl N-[cyclohexyl(imino)methyl]glycinate (830 mg) was dissolved in a solution (10%, 15 ml) of trifluoroacetic acid in 1,2-dichloroethane and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure. The residue was suspended in toluene, phosphorus oxychloride (3.21 ml) was added and the mixture was stirred at 80° C. for 30 min. DMF (2.67 ml) was added and the mixture was stirred at 100° C. for 5 hr. The reaction mixture was ice-cooled, basified by pouring into an aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object product (495 mg).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionphosphorus oxychloride (3.21 ml) was added
3. stirringthe mixture was stirred at 80° C. for 30 min
4. additionDMF (2.67 ml) was added
5. stirringthe mixture was stirred at 100° C. for 5 hr
6. temperaturecooled
7. additionby pouring into an aqueous sodium hydroxide solution
8. extractionextracted with ethyl acetate
9. washThe extract was washed with saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe solvent was evaporated under reduced pressure
12. washa fraction eluted with ethyl acetate-hexane (10:90-100:0)
13. concentrationwas concentrated under reduced pressure

ORD record

ord-87c9bdc5ec70409db30b20588f0a396f

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045436B2