Methanol → Methyl 2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-2-methylpropanoate

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Reaction Steps

250 mg (2.1 mmol) of 2-amino-3-methylhydroxypropanoic acid are dissolved in 9 ml of anhydrous MeOH. The reaction solution is cooled in an ice bath, and 0.153 ml (2.1 mmol) of SOCl2 is slowly added dropwise. The solution is allowed to reach room temperature slowly overnight. The reaction solution is concentrated in vacuo and then mixed with 1 ml of EtOAc and 5 ml of saturated NaHCO3 (aqueous), followed by 0.285 ml (1.995 mmol) of benzyl chloroformate. The solution is stirred at room temperature overnight. Then 5 ml of EtOAc are added, and the organic phase is separated off and washed twice with 1 ml of 1N HCl (aq) each time and twice with 2 ml of a saturated NaHCO3 (aq) each time, dried over MgSO4 and concentrated in vacuo. Purification took place by chromatography (40 g of SiO2, eluent MeOH/DCM (gradient 0-10%). The desired product is obtained as colorless oil (0.130 g) with MW=267 (calculated, monoisotopic), measured value: (M+Na)+ 290.

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