Hydrochloric Acid → (3S,5S)-3-amino-3,5-dimethyl-heptanoic acid

Temperature

40 °C

A mixture of (3S,5S)-3,5-dimethyl-3-((S)-2-methyl-propane-2-sulfinylamino)-heptanoic acid methyl ester (0.4 g, 1.37 mmol) and concentrated hydrochloric acid (7.6 mL) in acetone (10 mL) was refluxed for 3 hours. The solvents were stripped under reduced pressure. The residue was dissolved in water (10 mL) and extracted by EtOAc (2×15 mL). The aqueous phase was evaporated to dryness. The residue was dissolved in a mixture of water (10 mL) and triethylamine (0.5 mL). The mixture was stirred at 40° C. for 20 minutes and then was evaporated to dryness. The residue was washed thoroughly with acetonitrile, filtered, and dried under vacuum to give the final product, (3S,5S)-3-amino-3,5-dimethyl-heptanoic acid (0.182 g, 77% yield) as a white solid. m.p. 215–217° C.: 1H NMR (CDCl3) δ 4.85 (s, 3H), 2.38 (m, 2H), 1.75 (m, 1H), 1.39 (m, 4H), 1.35(s, 3H), 0.98 (d, J=6.6 Hz, 3H), 0.90 (t, J=7.5 Hz, 3H); MS (APCl) (M+1)+ 174.1.

1. temperaturewas refluxed for 3 hours
2. extractionextracted by EtOAc (2×15 mL)
3. customThe aqueous phase was evaporated to dryness
4. dissolutionThe residue was dissolved in a mixture of water (10 mL) and triethylamine (0.5 mL)
5. customwas evaporated to dryness
6. washThe residue was washed thoroughly with acetonitrile
7. filtrationfiltered
8. customdried under vacuum

ORD record

ord-3e83cc1a80e444acb5be55aad1da3fbe

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07179934B2