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

HRID 1440348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1440348
[OH:1][C@@H:2]1[C@H:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4](=[O:18])[CH2:3]1.[OH-:19].[Na+].Cl>CC(C)=O>[CH3:9][CH:8]([CH3:10])[CH2:7][C@H:6]([NH:5][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@@H:2]([OH:1])[CH2:3][C:4]([OH:18])=[O:19]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10901277(4S,5S)-4-hydroxy-5-isobutyl-1-t-butoxycarbonyl-2-pyrrolidinone

Produkt 1

HCID 2755962(3S,4S)-4-((tert-Butoxycarbonyl)amino)-3-hydroxy-6-methylheptanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-e2e11dedcfbe42978500d1db28c80a2c
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498732

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