Acetonitrile → HCID 86755903, compound

Participants

Reaction Conditions

Reaction Steps

(R)-N5 -(Cbz)-N2 -(diphenylacetyl)-(S)-N-[1-(4-bromophenyl)ethyl]ornithine amide (0.50 g; 0.78 mmol; from step (c) above) was suspended in CH2Cl2 :acetonitrile (20 mL; 1:3) and was cooled to 0° C. Trimethylsilyl iodide (0.17 g, 0.86 mmol) was added at 0° C. and the reaction stirred for 2 hours at 0° C. (solids dissolving as the reaction proceeded). When the deprotection was complete, as determined by TLC analysis, the reaction was quenched with water and diluted with EtOAc. The organic layer was separated and washed with water (1×), 1 N sodium thiosulfate (1×) and brine (2×). The combined aqueous washings were extracted with CH2Cl2. The organics were combined and triethylamine (5 mL) was added. The mixture was allowed to stand for 18 hours, transferred to a separating funnel, washed with brine (3×), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product as a yellow solid (0.40 g). The crude product was chromatographed on silica gel eluting with MeOH:CH2Cl2 (3:7), then MeOH:CH2Cl2 (1:1), to give sub-title compound (free base) as an off-white solid (0.25 g).

Provenance & Evidence