Sodium Chloride → HCID 11862697, compound

Participants

Reaction Conditions

Reaction Steps

An emulsion of 1.1 g racemic trans-4-Methylene-cyclopentane-1,2-dicarboxylic acid diethyl ester (Merck 8.14188.0010) in an aqueous buffer (potassium phosphate 5 mM, NaCl 0.1 M) was adjusted to pH 7.0. Under stirring at 7° C. the hydrolysis was performed with 14 mg lipase PN from Phycomyces nitens [Wako Chemicals GmbH Nissanstrasse 2 D-41468 Neuss Germany; catalog # 122-02651] under pH control (pH-stat, 1M NaOH). After consumption of 2.4 ml 1 M NaOH solution within 24 h the reaction mixture was extracted twice with 250 ml t-butyl methyl ether. The organic phase was subsequently washed with 250 ml saturated sodium bicarbonate and 250 ml saturated NaCl solution. Evaporation and drying in vacuo overnight yielded 0.49 g of the title compound 41a. MS: 226.0 (M)+; chiral GC: ee >99% (BGB-175, 30 m×0.25 mm; H2, 120 kPa, Split 1/20; 100-180° C., 2° C./min; Inj.-T.: 200° C.; Dect.-T.: 220° C.).

Provenance & Evidence