Sodium Hydroxide → (3R)-6-carboxy-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid

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Reaction Steps

Methyl (3R)-6-methoxycarbonyl-5-oxo-1-thia-4-azacyclotridecane-3-carboxylate (2.39 g, 7.21 mmol) is suspended in methanol (75 ml) and 1N sodium hydroxide (22.0 ml, 22.0 mmol) is added. The mixture is stirred for 4 hours at room temperature. The solvent is evaporated and the residue is dissolved in water (150 ml). The aqueous solution is adjusted to pH 1 by addition of 1 N hydrochloric acid and extracted with ethyl acetate (3×100 ml). The combined extracts are washed with brine (1×100 ml), dried (MgSO4) and the solvent is evaporated to give (3R)-6-carboxy-5-oxo-1-thia-4-azacyclotridecane-3-carboxylic acid, m.p. 167°-170° C.

Provenance & Evidence