Ammonia → HCID 178498182, compound

Participants

Reaction Steps

The methyl ester product from part (b) (2.3 g., 5.88 mmole) is suspended in acetone (7 ml.) at room temperature. Trimethylamine is bubbled in for about 20 minutes to saturate the mixture. The reaction vessel is sealed, and the mixture is heated to about 95° and is stirred overnight. The volatiles are evaporated, and the residue is partitioned between ethyl acetate and 5% potassium bisulfate. The organic layer is washed once with brine, dried (Na2SO4), filtered, and the volatiles are evaporated to give 1.86 g. of 4-[[(S)-2=[(hydroxymethylphosphinyl)oxy]-1-oxo-3-phenylpropyl]amino]benzoic acid, methyl ester. TLC (silica gel; isopropanol:ammonia:water, 7:2:1) Rf =0.62.

Provenance & Evidence