Methanol → (S,S)-alpha-[[3,3,3-Trifluoro-2-(mercaptomethyl)-1-oxopropyl]amino]cyclohexanepropanoic acid

Concentrated ammonium hydroxide (3.1 mL) was added to a suspension of the title (S) isomer product from part (a) (1.734 g., 4.69 mmol.) in deoxygenated water (3.1 mL) at room temperature. Dissolution occurred almost immediately and the reaction mixture was stirred for 10 minutes at room temperature. The pH was adjusted to 1.5 with saturated potassium bisulfate solution and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with brine, dried (MgSO4), and concentrated to a residue which was chromatographed on a 5×15 cm silica gel column. Elution with hexane: ethyl acetate:acetic acid, 80:20:2, concentration of the pure fractions, and coevaporation from heptane afforded a white solid which was triturated with hexane. This solid was dried under high vacuum for 18 hours to afford 1.28 g. of the title (S,S) isomer product; m.p. 141°-143° C., [α]D =+13.6° (c=0.85, methanol).

1. dissolutionDissolution
2. extractionthe mixture was extracted with ethyl acetate (200 mL)
3. washThe organic layer was washed with brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated to a residue which
6. customwas chromatographed on a 5×15 cm silica gel column
7. washElution with hexane
8. customethyl acetate:acetic acid, 80:20:2, concentration of the pure fractions, and coevaporation from heptane afforded a white solid which
9. customwas triturated with hexane
10. customThis solid was dried under high vacuum for 18 hours
11. customto afford 1.28 g

ORD record

ord-6d02a21ed76f4bbdb0b633cb1e0ef06d

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05414013