Ethylene Glycol → HCID 24802594, compound

Participants

Reaction Steps

Triethylamine (15 μL, 0.11 mmol) and ethyl chloroformate (15 μL, 0.16 mmol) were added sequentially to a solution of (Z)-7-[(1R,2S,3R,5R)-5-chloro-2-(3,5-dichloro-phenoxymethyl)-3-hydroxy-cyclopentyl]-hept-5-enoic acid (U.S. Provisional Patent Application No. 60/644,069, filed on Jan. 14, 2005, incorporated by reference herein, 10.5 mg, 0.025 mmol) in CH2Cl2 (0.2 mL) at room temperature. After 2.5 h, triethylamine (15 μL, 0.11 mmol) and ethylene glycol (200 μL, 3.59 mmol) were added. After stirring overnight at room temperature, the reaction mixture was partitioned between H2O (5 mL) and CH2Cl2 (5 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×5 mL). The combined organic phase was washed with 1 N HCl (5 mL) then dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (10% MeOH/CH2Cl2) afforded 2.5 mg (22%) of the title compound (1).

Provenance & Evidence