Water → (4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine

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Reaction Steps

To a mixture of (4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine HCl salt (Method C6a; 304 g, 0.8 mol), water (1 L) and EtOAc (1.4 L) was added NaHCO3 (150 g, 1.78 mol, 2.2 equiv.). The resulting mixture was stirred for 1 h. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The resulting viscous oil was treated with EtOH and concentrated under reduced pressure twice to afford (4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine as a low melting solid (264 g, 96%): mp 50° C.; [a]D=+2.4, (c 1.0, CH3OH); 1H NMR (CDCl3) 0.92-0.99 (m, 12H), 1.13 (t, J=7.4 Hz, 3H), 1.47-1.52 (m, 1H), 1.58-1.67 (m, 2H), 2.07-2.11 (m, 1H), 2.54 (q, J=7.4 Hz, 2H), 2.84-2.90 (m, 2H), 3.28 (dd, J=10.6, 6.6 Hz, 1H), 3.68 (dd, J=13.6, 8.1, Hz, 1H), 3.81-3.87 (m, 1H), 6.85 (d, J=7.9 Hz, 1H), 7.36-7.42 (m, 2H); CI-MS m/z 344 ((M+H)+).

Provenance & Evidence