Hydrochloric Acid → HCID 117628891, compound

Participants

Reaction Steps

To a solution of (2R)-2-amino-2-[5-(5,5-dimethyl-1,3-dioxan-2-yl)thiophen-2-yl]ethanol hydrochloride (11.54 g, 39.3 mmol) in DCM (262 mL) at 0° C. was added slowly triethylamine (25 mL, 179 mmol). The mixture was stirred 15 minutes, after which TMSCl (5.52 mL, 43.2 mmol) was added. The mixture was stirred for 30 minutes at 0° C. and then 1,3-benzothiazole-6-sulfonyl chloride (9.64 g, 41.2 mmol) was added. The reaction mixture was allowed to reach room temperature overnight, and then 1N HCl (100 mL) and MeOH (50 mL) were added and the reaction mixture was stirred for 2 hours. The organic layer was separated and the aqueous layer was extracted 5 times with ethyl acetate (5×300 mL). The organic layers were combined and washed twice with a saturated solution of sodium bicarbonate (2×250 mL), then washed with brine (250 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was swished with ether to obtain the pure desired product.

Provenance & Evidence