Sodium Carbonate → Methyl N-[hydroxy(phenoxy)methylidene]valinate

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Reaction Steps

To a solution of 100 g (596 mmol) of L-valine methyl ester hydrochloride and 84.92 g (542 mmol) of phenylchloroformate in 600 mL of water and 600 mL methylene chloride at 0° C. was added 139.0 g of Na2CO3 (1.311 mol) in portions. After addition was complete the cooling bath was removed and the solution was stirred at ambient temperature for one hour. The organic layer was separated, 1.0 mL of N,N-dimethylethylenediamine (11.0 mmol) was added to the organic layer and the solution mixed for three minutes. The organic layer was washed with 100 mL of 1M potassium hydrogen sulfate solution. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford 135.65 g of the title compound as white crystalline solid; mp 59.1° C.

Provenance & Evidence