Triethylamine → HCID 13621772, compound

Participants

Reaction Steps

Compound XXXI (2.71 g, 0.007 mL) was dissolved in CH2Cl2 (25 mL), cooled and Et3N (0.78 g, 0.0077 mol) added. To the cooled solution, methanesulfonyl chloride (0.88 g, 0.0077 mol) in CH2Cl2 (2 mL) was added and stirred at room temperature. After 3 hours another portion of methanesulfonylchloride (0.09 g, 0.007 mol) was added. After 1 hour, the reaction was poured in H2O (25 mL) containing K2CO3 (1 g) and the organic extracted with CH2Cl2 (3X). The aqueous extracts were washed with H2O, 0.5N, HCl, H2O, dried, filtered and concentrated to dryness. The residue was dissolved in dry DMSO (20 mL) and added with stirring at room temperature to a solution of XXX (1.7 g, 0.005 mol) and NaH (60% oil dispersion, 0.22 g, 0.0055 mol) in DMSO (20 mL). After 2 hours, another portion of NaH (0.2 g) was added and stirred at room temperature for an additional 2 hours. The solution was then poured in H2O and the aqueous extracted with EtOAc (2X). The organic extracts were dried, filtered and concentrated to dryness. The residue was treated with CH3OH (25 mL) and 40% NaOH (6 mL) and the solution heated at reflux. After 2 hours, the solution was poured into H2O. The aqueous layer was extracted with CHCl3 (3X) and the organic extracts dried, filtered and concentrated to dryness. The residue was treated with CH3OH (50 mL) and HOAc (2.5 mL) and heated at reflux for 2 hours. The reaction was then concentrated to dryness, 0.1N HCl (75 mL) added, the aqueous extracted with CHCl3 (3X) and the organic extracts discarded. The aqueous solution was basified to pH 10 with saturated Na2CO3 and extracted with CHCl3 (2X). The organic extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel eluting with CHCl3 saturated with NH3 and CHCl3 --CH3OH--NH4OH (70:5:0.5 to 90:10:1) to yield XXXII; 13% yield.

Provenance & Evidence