Hydrochloric Acid → 5-(3-((1R,2R,3R,5R)-5-Chloro-2-((3S 8R,E)-3,8-dihydroxynon-1-en-1-yl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylic acid

Participants

Reaction Steps

Lithium hydroxide (1.2 mL of a 0.5N solution in H2O, 0.605 mmol) was added to a solution of the ester 31 (111 mg, 0.242 mmol) in THF (0.5 mL) at 23° C. After stirring for 24 h the reaction mixture was acidified with 1N HCl and extracted with EtOAc. The organic portion was washed with brine (2×), dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 4:1 CH2Cl2/MeOH) provided 90 mg (84%) of the free acid 33 (see Scheme 5).

Provenance & Evidence