Methanol → 7-[2-(3-Hydroxyoctyl)-4-oxo-3-thiazolidinyl]heptanoic acid

Participants

Reaction Conditions

Reaction Steps

A turbid mixture of methyl 7-[2-(3-acetyloxyoctyl)-4-oxo-3-thiazolidinyl]heptanoate (785 mg., 1.89 milimole), 2.5 N aqueous sodium hydroxide (2ml.), and methanol (6 ml.) is stirred at 25° C. for 15 hours. After removing the solvents in vacuo below 50° C., the residual mass is acidified with 2 N hydrochloric acid and extracted twice with ether. The combined organic extract is washed with water, dried over magnesium sulfate, and filtered. In vacuo evaporation of the filtrate provides an oily residue which is applied to a silica gel column (20 g.) with chloroform. Elution with chloroform-acetic acid (50:1; v:v; 200 ml.) affords impure product; continued elution with the same eluant (600 ml.) provides the title compound as a pale yellow oil (494 mg., 73%); pmr (CDCl3) δ 0.90 (3H, t), 2.34 (2H, t), 2.60--3.30 (H,m), 3.30--4.00 (4H, m, containing a singlet at 3.54), 4.53--4.93 (H, m) and 7.10 (2H, broad s, D2O exchangeable). Anal. Calcd. for C18H33NO4S: C, 60.13; H, 9.25; N, 3.90. Found: C, 59.87; H, 9.11; N, 3.55.

Provenance & Evidence