Hydrochloric Acid → (3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid

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Reaction Steps

1 g of this 4-hydroxy-2-pyrrolidinone is dissolved in 5 ml of acetone. 2 ml of 1M sodium hydroxide are added dropwise. After 2 hours, the reaction mixture is acidified carefully with dilute hydrochloric acid to pH 3-4. The Boc-statine obtained is precipitated by adding water, drained, washed with water and then with hexane and dried under vacuum in the presence of potassium hydroxide pellets. 810 mg of this statine are thus obtained, in the form of a white solid having the following characteristics: mp=120°-120° C.; Rf=0.52 (eluent CHCl3 /MeOH/AcOH: 180/10/5); [α]D20 =+41.9°(c=1,MEOH); 1HNMR(DMSO-d6) δ ppm: 0.85(6H,dd,CH3); 1.26(2H,m,CH2); 1.37(9H,s,Boc); 1.55(1H,m,CH); 2.21(2H,m,H-2); 3.51(1H,m,H-4); 3.80(1H,m,H-3); 6.31(1H,d,NH); MS-FAB+: 276.

Provenance & Evidence