Sodium hydride → HCID 117871254, compound

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Reaction Steps

In a 100 mL round-bottomed flask, (S)-2-(benzyloxycarbonylamino) propanoic acid (1 g, 4.48 mmol, Eq: 1.00) was combined with DMF (9 mL) to give a colorless solution. Sodium hydride (394 mg, 9.86 mmol, Eq: 2.2) was added. After 30 min, 1-bromo-2-methoxyethane (747 mg, 505 μL, 5.38 mmol, Eq: 1.2) was added and the reaction was stirred at rt overnight. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with water and brine then dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 10% MeOH in DCM) to give (S)-2-[benzyloxycarbonyl-(2-methoxy-ethyl)-amino]-propionic acid (0.15 g).

Provenance & Evidence