Toluene → 5'-((1R,2R)-1-Benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-2'-fluoro-biphenyl-2-carboxylic acid t-butyl ester

Participants

Reaction Conditions

Reaction Steps

2-t-Butoxycarbonylphenylboronic acid pinacol ester (173 mg, 568 μmol, 1.2 eq.) and toluene (661 μL) were added to (2R,3R)-3-(3-bromo-4-fluoro-benzoylamino)-2-hydroxy-4-phenyl-butyric acid ethyl ester (201 mg, 474 μmol, 1.0 eq.), followed by EtOH (361 μL) then K2CO3 (131 mg, 947 μmol, 2.0 eq.) predissolved in water (124 μL). The mixture was stirred to aid in dissolution. The reaction vessel was purged with nitrogen then Pd(PPh3)4 (54.7 mg, 47.4 μmol) was added quickly. The reaction vessel was capped and heated to 100° C. for 30 minutes. The organics were removed and evaporated under vacuum to yield 5′-((1R,2R)-1-benzyl-2-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-2′-fluoro-biphenyl-2-carboxylic acid t-butyl ester.

Provenance & Evidence