Triethylamine → HCID 57052419, compound

Participants

Reaction Steps

The mono ester product from part (e) (0.81 g., 1.94 mmole) in tetrahydrofuran (4 ml.) at 0° in an argon atmosphere was treated with carbonyldiimidazole (0.31 g., 1.0 eq.). After one hour, triethylamine (0.3 ml., 1.1 eq.) then L-proline, t-butyl ester (0.43 g., 1.3 eq.) were added to the above mixture. After stirring at room temperature for 16 hours, the reaction mixture was diluted with ethyl acetate and then washed with water, 5% sodium bicarbonate, 5% potassium bisulfate (twice), brine, dried (MgSO4), and evaporated to give 0.9 g of 1-[[ethoxy[3-phenyl-2-[[(phenylmethoxy)carbonyl]amino]propyl]phosphinyl]acetyl]-L-proline, 1,1-dimethylethyl ester as a foam. Tlc (dichloromethane/acetic acid/methanol; 100/5/5) major spot at Rf =0.5.

Provenance & Evidence