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

HRID 1440348Notes

Reaction equation

HRID 1440348 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Sources & evidence

ORD record
ord-e2e11dedcfbe42978500d1db28c80a2c
Source dataset
uspto-grants-1996_03
Patent number
US05498732

Reaction notes

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