Diisopropylethylamine → 3,5-Dichlorobenzyl 2-(2-(2-oxo-2,3-dihydrooxazole-5-carboxamido)ethyl)morpholine-4-carboxylate

A mixture comprising of 3,5-dichlorobenzyl 2-(2-aminoethyl)morpholine-4-carboxylate (Example 11, step 2) (178 mg, 0.534 mmol), 2-oxo-2,3-dihydrooxazole-5-carboxylic acid (Example 21, step 1) (68.9 mg, 0.534 mmol), T3P® (50% in DMF) (510 mg, 0.801 mmol), Huenig's base (466 μl, 2.67 mmol) in DMF (1781 μl) was stirred at room temperature. Another 1 equivalent of 2-oxo-2,3-dihydrooxazole-5-carboxylic acid was added and the reaction mixture was left stirring at room temperature overnight. The resulting reaction mixture was concentrated under reduced pressure and the crude product was diluted with EtOAc. The organic portion was dried with MgSO4, filtered and concentrated under reduced pressure. The crude material was dried loaded using silica onto an ISCO 4 g column eluting with 0-100% EtOAc (1% acetic acid) in iso-hexane. The product fractions were concentrated under reduced pressure to afford the title compound;

1. waitthe reaction mixture was left
2. customThe resulting reaction mixture
3. concentrationwas concentrated under reduced pressure
4. additionthe crude product was diluted with EtOAc
5. dry with materialThe organic portion was dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. dry with materialThe crude material was dried
9. washeluting with 0-100% EtOAc (1% acetic acid) in iso-hexane
10. concentrationThe product fractions were concentrated under reduced pressure

ORD record

ord-fa4a7d074d16437485ec2946b23613fd

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409895B2