Potassium Carbonate → HCID 91615104, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Boc-Tyr-OMe (0.80 g, 2.7 mmol), 4-fluorobenzophenone (0.80 g, 4.0 mmol) and potassium carbonate (1.11 g, 8.0 mmol) in DMF (30 mL) was heated to 100° C. After 42 h, the reaction mixture was allowed to cool to rt. DMF was removed in vacuo and the remaining material was partitioned between EtOAc (50 mL) and water (50 mL). This gave an emulsion that was allowed to sit overnight. The following day the layers had mostly separated and so the organic layer was concentrated in vacuo to give 1.32 g of material. This material was purified by chromatography (4:1 hexane/ethyl acetate) to give 0.69 g of product. 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9H), 2.98-3.19 (m, 2H), 3.74 (s, 3H), 4.60 (q, J=6.8 Hz, 1H), 5.03 (br d, J=7.6 Hz, 1H), 6.98-7.05 (m, 4H), 7.14-7.19 (m, 2H), 7.45-7.51 (m, 2H), 7.55-7.61 (m, 1H), 7.75-7.84 (m, 4H).

Provenance & Evidence