1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86700688, compound

A solution of (2S,5R)-6-(benzyloxy)-2-(5-(piperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (2.0 g, 7.25 mmol), EDCI (1.53 g, 7.98 mmol) and HOBT (1.08 g, 7.98 mmol) in DMF (15 mL) was stirred at rt for 0.5 h. 1-Hydroxyguanidine (0.653 g, 7.98 mmol) was then added and the reaction mixture was stirred for an additional 0.5 h. The resulting solution was treated under microwave at 100° C. for 1.5 hrs. The mixture was poured into water and extracted with EtOAc (2×). The combined organic layers were then washed with water (20 mL), and saturated sodium chloride (20 mL), dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (2:1 EtOAc/petroleum ether) to give (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (1.0 g, 44%). (ESI-MS (EI+, m/z): 316 [M+H]+.

1. additionThe resulting solution was treated under microwave at 100° C. for 1.5 hrs
2. extractionextracted with EtOAc (2×)
3. washThe combined organic layers were then washed with water (20 mL), and saturated sodium chloride (20 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by silica gel column chromatography (2:1 EtOAc/petroleum ether)

ORD record

ord-d3d85a93c60e4eb29540b4fced52d09e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916709B2