Ethyl bromoacetate → HCID 67435462, compound

Temperature

0 °C

To a stirred solution of Intermediate 19 (210 mg) in anhydrous N,N-dimethylformamide (3 mL) at 0° C. under an atmosphere of nitrogen was added sodium hydride (40.4 mg) as a 60% by weight suspension on mineral oil in one charge. The reaction mixture was stirred at 0° C. for 30 min. To the reaction mixture was added neat ethyl bromoacetate (0.105 mL) in one charge the reaction was then left stirring at 0° C. for 1 hour and then warmed to ambient temperature and left stirring under nitrogen atm. for 1 hour. The RM was cooled down to 0° C., sodium hydride (40.4 mg) as a 60% by weight suspension on mineral oil was then added in one charge. The reaction mixture was stirred at 0° C. for 30 min. To the reaction mixture was again added neat ethyl bromoacetate (0.105 mL) in one charge the reaction was gradually warmed to ambient temperature under nitrogen atm. overnight. The RM was concentrated under vacuum. The residue was purified by MDAP (Method B). The desired fractions were combined and concentrated under nitrogen blowdown to give the title compound (61 mg).

1. additioncharge
2. additioncharge the reaction
3. waitwas then left
4. stirringstirring at 0° C. for 1 hour
5. temperaturewarmed to ambient temperature
6. waitleft
7. stirringstirring under nitrogen atm
8. waitfor 1 hour
9. temperatureThe RM was cooled down to 0° C.
10. additioncharge
11. stirringThe reaction mixture was stirred at 0° C. for 30 min
12. additioncharge the reaction
13. temperaturewas gradually warmed to ambient temperature under nitrogen atm
14. customovernight
15. concentrationThe RM was concentrated under vacuum
16. customThe residue was purified by MDAP (Method B)
17. concentrationconcentrated under nitrogen

ORD record

ord-79533b4ef7fd44498826a4c41fc2745a

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399444B2