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-cd43d51a6b0340a189717f8b211c80f6

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05414017