Ammonia → HCID 18759733, compound

To a stirred solution of 1.21 g (7.02 mmol) of Part A(4) compound in 50 mL of toluene was added 3 mL (134 mmol) of oxalyl chloride. The reaction mixture was stirred for 1 hour at room temperature under argon and then 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 of the crude acid chloride was stirred in 5 mL of methanol and then 1.17 mL (8.43 mmol) of triethylamine and 2 mL (9M, 18 mmol) of methanolic ammonia were added at room temperature under argon. After stirring for 16 hours, the reaction mixture was partitioned between 3 mL water and 20 mL ethyl acetate. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate (20 mL). The combined organic layers were washed with brine then dried (magnesium sulfate) 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 title compound 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 of the crude acid chloride was stirred in 5 mL of methanol
6. stirringAfter stirring for 16 hours
7. customthe reaction mixture was partitioned between 3 mL water and 20 mL ethyl acetate
8. customThe organic layer was separated
9. extractionthe aqueous layer was extracted twice with ethyl acetate (20 mL)
10. washThe combined organic layers were washed with brine
11. dry with materialthen dried (magnesium sulfate)
12. concentrationconcentrated in vacuo
13. customto obtain a semi-solid
14. customThe semi-solid was crystallized by trituration with hexane

ORD record

ord-9cced3e0e66647ca86d0f12c6d6cd00c

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05153327