Chloroform → N-Boc-N-methyl-4-methoxy-L-phenylalanine

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Reaction Steps

To a solution of BOCTyr-OH (0.562 g, 2 mmol) in dry THF at 0° C. CH3I (2.8 g, 20 mmol) and NaH (0.24 g, 10 mmol) were added with vigorous stirring. The reaction mixture was stirred at r.t. for 24 hrs., then chilled, and NaH was destroyed by added EtOAc with water. The clear solution was evaporated to dryness and the residue was taken up in 10 ml of water. The aqueous solution was extracted with ether (2×10 ml), acidified with citric acid and extracted with EtOAc. The organic layer was washed with 5% hypo solution and water, dried over Na2SO4 and evaporated to dryness. The product was obtained as an oil: yield 0.56 g (91%); FABMS m/z 310 (M+H): 10. 0.5:0.5 Rf 51 (CHCl3 : MeOH: AcOH); Anal. Calcd. for C16H24NO4 : Mr 310.1663 (M+H); Found: Mr 310.1654 (M+H) (HRFABMS).

Provenance & Evidence