Propyl mercaptan → HCID 53240650, compound

Participants

Reaction Steps

A mixture of lithium hydride (0.88 g, 110 mmol), 1-propanethiol (11.7 mL, 133 mmol) in HMPA (20 mL) was prepared under N2. The mixture was stirred at room temperature for 30 min. To the mixture, (1R,10S,11S,16S)-5-methoxy-11,15,15-trimethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-3-carboxylate (64) (4.8 g, 11 mmol) in HMPA (10 mL) was added. The mixture was heated at 130° C. for 1 h. The mixture was cooled to room temperature and quenched with 1 M HCl, then extracted with EtOAc. The organic layer was concentrated to dryness. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH, 10:1) to yield (1R,10R,11S,16S)-5-hydroxy-1,11,15,15-tetramethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]-octadeca-2,4,6-triene-3-carboxylic acid (65) (4.2 g, 93%) as a white solid. 1H NMR (CD3OD): δ 7.18 (s, 1H), 6.88 (s, 1H), 3.45 (m, 1H), 2.83 (m, 1H), 2.10 (d, 1H), 1.82-1.35 (m, 10H), 1.20 (m, 2H) 1.00 (m, 5H), 0.89 (s, 3H), 0.85 (s, 3H). MS m/z 405 (C22H30NO5S−H+).

Provenance & Evidence