Hydrochloric Acid → HCID 86614676, compound

To a stirred mixture of N-(trifluoroacetyl)-L-alanine (5.05 g, 27.3 mmol) and pyridine (0.3 mL) was added oxalyl chloride (7.62 g, 60 mmol) at 0° C. under a nitrogen atmosphere. The reaction mixture was then allowed to warm to room temperature and stirred for an additional 2 hrs. The reaction mixture was then concentrated under reduced pressure to provide an oil that was combined with 8 mL of thioanisole. The resulting solution was then added a solution of AlCl3 (76 mmol, about 2.8 eq. relative to the N-(trifluoroacetyl)-L-alanine, about 10 g) in thioanisole (7 mL) at 0° C. The resulting reaction mixture was then allowed to warm to room temperature and stirred for about 14 hrs. After stirring, the reaction mixture was poured into cold 1 N aqueous hydrochloric acid (200 mL) and the resulting mixture extracted with ethyl acetate (200 mL), the ethyl acetate dried (Na2SO4), and the ethyl acetate removed under reduced pressure to provide a residue that was purified by flash chromatography using a silica gel column eluted with ethyl acetate/hexane in a ratio of 1:9 to provide S (−)-2-[N-(trifluoroacetyl)amino]-1-(4-methylthiophenyl)-1-propanone (B) (35% yield).

1. concentrationThe reaction mixture was then concentrated under reduced pressure
2. customto provide an oil that
3. customThe resulting reaction mixture
4. temperatureto warm to room temperature
5. stirringstirred for about 14 hrs
6. stirringAfter stirring
7. extractionthe resulting mixture extracted with ethyl acetate (200 mL)
8. dry with materialthe ethyl acetate dried (Na2SO4)
9. customthe ethyl acetate removed under reduced pressure
10. customto provide a residue that
11. customwas purified by flash chromatography
12. washeluted with ethyl acetate/hexane in a ratio of 1:9

ORD record

ord-f46bc08680f4424d9b215580908805db

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07518017B2