Dimethylformamide → HCID 140401819, compound

Participants

Reaction Steps

A solution of 211 (100 mg, 0.38 mmol) in methanol was treated with 10% Pd-C (50 mg) and was shaken under 60 psi H2 in a Paar apparatus. The catalyst was filtered (celite) and solvent was evaporated to afford a solid residue which was dissolved in DMF (2.5 mL). To this solution was added bis-Boc-thiourea (113 mg, 0.42 mmol), and Et3N (111 mL, 0.80 mmol). The DMF solution was cooled to 0° C., HgCl2 (114 mg, 0.42 mmol) was added, and the mixture was stirred at 0° C. for 3 h then at rt for 20 h. The crude product was isolated in the same manner as described for Example 201 and was chromatographed on silica gel (1/1-ethyl acetate/hexane) to afford bis-Boc-guanidine 212 (145 mg, 79%) as a colorless glass: 1H NMR (300 MHz, CDCl3) d 1.25 (t, 3H, J=7.6), 1.49 (s, 9H), 1.55 (s, 9H), 2.16 (s, 3H), 2.68 (q, 2H, J=7.6), 3.91 (s, 3H), 7.86 (d, 1H, J=1.5), 8.05 (d, 1H, J=1.5), 8.76 (s, 1H), 10.46 (s, 1H), 11.54 (s, 1H).

Provenance & Evidence