Ammonia → HCID 18759733, compound

To a stirred solution of Part C acid (1.21 g, 7.02 mmol) in 50 mL of toluene was added 3 mL of oxalyl chloride. This reaction mixture was stirred for 1 hour at room temperature under argon and concentrated in vacuo. The residue was diluted with 20 mL of toluene and concentrated again. This was repeated to remove traces of oxalyl chloride. The residue was stirred at room temperature under argon in 5 mL of CH3OH and (C2H5)3N (1.17 mL, 8.43 mmol), and an excess of 9 M methanolic ammonia (2 mL) was added. After stirring for 16 hours, the reaction mixture was partitioned between 3 mL water and 20 mL EtOAc. The aqueous layer was extracted twice more with EtOAc (20 mL). The combined organic layers were washed with NaCl, dried over MgSO4, filtered, and concentrated in vacuo to obtain a semi-solid. The semi-solid was crystallized by trituration with hexane to obtain 0.5 g (42 %) of the desired title product as a solid.

1. concentrationconcentrated in vacuo
2. additionThe residue was diluted with 20 mL of toluene
3. concentrationconcentrated again
4. customto remove traces of oxalyl chloride
5. stirringThe residue was stirred at room temperature under argon in 5 mL of CH3OH
6. stirringAfter stirring for 16 hours
7. customthe reaction mixture was partitioned between 3 mL water and 20 mL EtOAc
8. extractionThe aqueous layer was extracted twice more with EtOAc (20 mL)
9. washThe combined organic layers were washed with NaCl
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customto obtain a semi-solid
14. customThe semi-solid was crystallized by trituration with hexane

ORD record

ord-2b13ce7ca59d413e8993185bc11286d3

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05153327