(2S,3R)-3-(benzyloxy)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)butanoic acid → (3S)-N-(4-Ethynyl-2-fluoro-phenyl)-2-{(R)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide

Participants

Reaction Steps

Prepared by the same method as described in example 48 except that (i) after step 3, and prior to step 4, (2S,3S)-2-amino-N-(2-fluoro-4-iodo-phenyl)-3-phenyl-butyramide was converted to (2S,3S)-2-amino-N-(2-fluoro-4-trimethylsilanylethynyl-phenyl)-3-phenyl-butyramide under the conditions described below, and (ii) after initial purification in step 6 the product was subjected to chiral HPLC separation as described below. The trimethylsilyl group introduced in step 3 was subsequently removed during step 5 of the synthesis, concomitant with removal of the tert-butyloxycarbonyl protecting group.

Provenance & Evidence