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

HRID 1440348ノート

反応式

HRID 1440348 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-e2e11dedcfbe42978500d1db28c80a2c
出典データセット
uspto-grants-1996_03
特許番号
US05498732

反応ノート

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