N-OCTYL L-2-PYRROLIDONE-5-CARBOXYLATE synthesis

Yield:4931-70-8 100%

Reaction Conditions:

Novozym 435 at 60; under 15.0015 Torr; for 24 h;Enzymatic reaction;

Steps:

4 Preparation of Octyl Pyroglutamate

In a multinecked round-bottomed flask, 50.0 g (336 mmol) of a mixture of ethyl pyroglutamate and pyroglutamic acid (molar ratio 71:29) and 43.7 g (336 mmol) of octanol as initial charge were heated to 60° C. After adding 4.6 g of Novozym 435 (immobilized lipase B from C. antarctica), a vacuum was applied (20 mbar) and low-boiling reaction products were distilled off. The reaction was monitored by means of NMR spectroscopy or by means of a suitable chromatographic method. Conversion after 8 hours: 95%, after 24 hours: >98%. When the reaction was complete, the immobilized enzyme was filtered off. The filtrate gave 81 g of product (100% of the theoretical yield) without further work-up as a pale yellow liquid. ¹H NMR (DMSO-d₆, 400 MHz): δ=8.0 (br, s, 1H), 4.2 (dd, ³J=8.6 Hz, 4.3 Hz, 1H), 4.1 (t, ³J=6.5 Hz, 2H), 2.3 (m, 1H), 2.1 (m, 2H), 2.0 (m, 1H), 1.6 (m, 2H), 1.3 (m, 10H), 0.8 (t, ³J=7.1 Hz, 3H).

References:

US2006/74259,2006,A1 Location in patent:Page/Page column 3