Nitrogen → HCID 66750659, compound

Participants

Reaction Steps

To a solution of 5-(3,6-bis-benzyloxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt (0.129 g, 0.252 mmol) in H2O (5 mL), flushed with N2, is added 10% Pd/C (0.10 g). The mixture is flushed with N2 again and then placed under an atmosphere of H2. The mixture is stirred vigorously for 1.5 h before being judged complete by LC/MS. The reaction mixture is filtered over Celite. The filtrate is washed with EtOH and the aqueous layer is lyophilized overnight. The residual solid is redissolved in H2O and refiltered over Celite. The green filtrate is lyophilized again overnight. The residue is purified via prep HPLC. The desired fractions are concentrated and dissolved in a minimum amount of EtOH. To this solution is added a 0.5M solution of KHCO3 followed by the addition of H2O. The reaction mixture is stirred for 2 min and lyophilized overnight to afford 5-(3,6-dihydroxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt: 1H NMR (DMSO-d6) 9.93 (s, 1H), 9.63 (s, 1H), 7.79 (s, 1H), 7.61 (d, J=8 Hz, 1H), 7.01 (s, 1H), 6.86 (m, 2H), 4.43 (s, 2H).

Provenance & Evidence