Dichloromethane → chloromethyl (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoate

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Reaction Steps

To a mixture of (S)-2-(t-butoxycarbonylamino)-3-methylbutanoic acid (28.6 g, 130 mmol) and NaHCO3 (44 g, 520 mmol) and Bu4NHSO4 (4.4 g, 13 mmol) in DCM (200 mL) and water (200 mL) was added chloromethyl sulfochloridate (26 g, 158 mmol) at 0° C. The mixture was stirred at room temperature for 24 hours, and then was extracted with DCM (3×150 mL). The combined organic layers were washed with water (2×300 mL), and the DCM layer was purified by flash column (PE:EtOAc=15:1) to yield the title compound as a yellow solid (35 g). LC-MS: 266 [M+H]+.

Provenance & Evidence