Bromoacetic Acid → HCID 68584488, compound

Temperature

60 °C

Compound 25B (2.17 g, 13.2 mmol) in 40 mL of dichloromethane was treated with a premixed solution of 1,3-dicyclohexylcarbodiimide (3 g, 14.5 mmol) and bromoacetic acid (1.84 mg, 13.2 mmol) in 30 mL of dichloromethane. The reaction was stirred for 1 hour and then quenched with 50 mL of water and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and excess solvent removed via rotary evaporator. The crude product was then dissolved in 30 mL of DMSO and potassium carbonate (2.27 g, 16.5 mmol) was added to the mixture. The reaction was heated to 60° C. overnight then cooled and poured oven ice water. The resulting precipitate was collected be filtration to give 200 mg (7%) of desired product. MS (electrospray): mass calculated for C12H16N2O, 204.13; m/z found 205.1, [M+H]+.

1. customquenched with 50 mL of water
2. extractionextracted with dichloromethane (3×50 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customexcess solvent removed via rotary evaporator
7. dissolutionThe crude product was then dissolved in 30 mL of DMSO
8. temperaturethen cooled
9. customThe resulting precipitate was collected
10. filtrationfiltration

ORD record

ord-7f855aa7559b47b9ae952bbc5a08ea21

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723326B2