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

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 (APCI) (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 기록

ord-2ec39482df8b4ee1a5060a0c6f58fbcc

출처 데이터셋

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07388023B2