Triethylamine → 3,5-Dichlorobenzyl 2-(2-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)(methyl)amino)ethyl)morpholine-4-carboxylate

A mixture comprising of 3,4-diethoxycyclobut-3-ene-1,2-dione (29.0 μl, 0.196 mmol) and triethylamine (1093 μl, 7.84 mmol) in EtOH (654 μl) was stirred at 40° C. for 20 minutes. The reaction was allowed to cool back to room temperature and 3,5-dichlorobenzyl 2-(2-(methylamino)ethyl)morpholine-4-carboxylate (Example 13, step 2) (68.1 mg, 0.196 mmol) was added. The reaction mixture was allowed to stir at room temperature for 16 hours. The resulting reaction mixture was concentrated under reduced pressure and purification was carried our using preparative LC-MS. The resulting product fractions were concentrated under reduced pressure to give an aqueous solution and then extracted with EtOAc. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound;

1. customThe resulting reaction mixture
2. concentrationwas concentrated under reduced pressure and purification
3. concentrationThe resulting product fractions were concentrated under reduced pressure
4. customto give an aqueous solution
5. extractionextracted with EtOAc
6. dry with materialThe organic extracts were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-0fe834e4384c4d4191ee6c4868a5da4d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409895B2