Triphenylphosphine → HCID 86757014, compound

Participants

Reaction Conditions

Reaction Steps

This was prepared in a two step sequence. A solution of Boc-homophenylalanyl-Nδ-Boc-Nα-methylornithinol (D) (392 mg) and 2-mercaptobenzothiazole (267 mg) in dry tetrahydrofuran (9 ml) was cooled to 0° C. under nitrogen atmosphere. Then, a solution of triphenylphosphine (1.04 g), anhydrous tetrahydrofuran (1 ml), and diethyl azodicarboxylate (620 μl) was added. The reaction mixture was stirred for 1.5 h at 0° C., concentrated in vacuo, and purified by flash chromatography (30% ethyl acetate/hexane) to give Boc-homophenylalanyl-Nδ-Boc-Nα-methylornithinyl 2-benzo-thiazolyl thioether (270 mg). This intermediate was deprotected by Procedure E to afford titled product (75 mg): HPLC [20 to 40% gradient (acetonitrile/0.1% TFA) over 60 min, retention time=42.96 min]; 1H NMR (400 MHz, D2O) δ1.49 (m, 2H), 1.83 (m, 2H), 1.98 (m, 1H), 2.18 (m, 1H), 2.79 (m, 2H), 2.82 (s, 3H), 3.09 (m, 2H), 3.57 (dd, J=14.8; 11.2 Hz, 1H), 3.70 (dd, J=14.8; 4.0 Hz, 1H), 4.46 (m, 1H), 5.01 (m, 1H), 7.17 (m, 2H), 7.38 (m, 3H), 7.49 (t, J=8.0 Hz, 1H), 7.61 (t, J=7.2 Hz, 1H), 7.91 (d, J=8.0 Hz, 1H), and 7.94 (d, J=8.4 Hz, 1H).

Provenance & Evidence