Benzoyl chloride → HCID 17751500, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(3-hydroxy-7,7-dimethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt (47 mg, 0.14 mmol; prepared from the title compound of Example 49 analogously to procedure as described in Example 1, step I) in DMF (3 mL) at 0° C. is added potassium t-butoxide (1M in THF, 0.13 mL,). After 5 min, benzoyl chloride (0.016 mL, 0.14 mmol) is added. The mixture is stirred at 0° C. for 5 min. The mixture is partitioned between Et2O and aq. K2CO3. The ether layer is removed. The aqueous layer is acidified by adding 3M HCl solution, and Et2O is added to extract the product. The organic residue is purified by HPLC to give the title compound as a solid: 1H NMR (CD3OD) δ 1.02 (s, 6H), 1.62 (t, J=7 Hz, 2H), 2.59 (s, 2H), 2.88 (t, J=7 Hz, 2H), 4.43 (s, 2H), 7.11 (s, 1H), 7.23 (s, 1H), 7.52-7.55 (m, 2H), 7.65-7.69 (m, 1H), 8.16-8.19 (m, 2H); (M+H)+=413.

Provenance & Evidence