Trifluoroacetic acid → HCID 67151550, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of trifluoroacetic acid (4.9 ml) in water (24 ml) was added (S)-2,2-dimethyl-4-[(E)-2-(4-nitro-phenyl)-vinyl]-oxazolidine-3-carboxylic acid tent-butyl ester (Example 14(a)) (5.0 g) in acetonitrile (4.0 ml). After stirring at 80° C. for 4 hours, the reaction mixture was cooled to room temperature and the solution basified to pH>11 by dropwise addition of a 1N solution of sodium hydroxide The mixture was extracted three times with ethyl acetate, the combined organic layers were dried (MgSO4) and concentrated in vacuo to yield (E)-(S)-2-Amino-4-(4-nitro-phenyl)-but-3-en-1-ol as a brown oil (2.5 g). 1H-NMR (300 MHz, CDCl3, δ); 8.23-8.11 (m, 2H), 8.54-8.47 (m, 2H), 7.67 (d, J=16 Hz, 1H), 6.7 (dd, J=16 and 8 Hz, 1H). 3.78-3.69 (m, 2H), 3.58-3.42 (m, 1H).

Provenance & Evidence