L-Threonine → (Methoxycarbonyl)-L-threonine

반응식

[OH-].[Na+].[NH2:3][C@H:4]([C:8]([OH:10])=[O:9])[C@@H:5]([CH3:7])[OH:6].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:18]([O:20][CH3:21])=[O:19]>>[OH:6][C@H:5]([CH3:7])[C@H:4]([NH:3][C:18]([O:20][CH3:21])=[O:19])[C:8]([OH:10])=[O:9]

참가 물질

반응물 4

HCID 6288L-Threonine

HCID 6586Methyl chloroformate

HCID 10340Sodium Carbonate

HCID 14798Sodium Hydroxide

생성물 1

HCID 28377863(Methoxycarbonyl)-L-threonine수율 538.6%

반응 조건

온도: 0 °C

실험 절차

An aqueous NaOH (1 M, 167 mL) solution is added, while stirring, to L-Threonine (20 g, 30.5 mmol) in a round bottom flask (1 L). To this solution was added sodium carbonate (9.8 g, 92.3 mmol). The flask is cooled to 0° C. in an ice-water bath. Methyl chloroformate (14.3 mL, 184.7 mmol) is added drop wise and the reaction mixture is allowed to stir for 15 hours and reach room temperature. The reaction mixture is washed with CH2Cl2 (3×50 mL), and the aqueous layer is contained in a round bottom flask and cooled over an ice-water bath. Concentrated HCl (aq) is added drop wise until pH 2. The aqueous solution is brought to room temperature and the water is removed in vacuum. The residue was taken up in a 2:1 mixture of MeOH/CH2Cl2 (150 mL, filtered and washed with 2:1 mixture of MeOH/CH2Cl2 (50 mL). The filtrate was concentrated and dried in vacuum at 40° C., resulting in white foam (29.1 g, 98%).