Methyl Acetate → HCID 68173591, compound

Participants

Reaction Conditions

Reaction Steps

(4R,6S)-6-(Chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid methyl ester (Compound B, 47.2 g, 0.20 mol) was dissolved in 150 mL of N-methylpyrrolidone. Then NaHCO3 (23.5 g, 0.28 mol) and tetra-n-butyl ammonium bromide (0.5 g) were added. To the stirred mixture was added 1-methyl-1H-tetrazole-5-thiol (MTT, 27.8 g, 0.24 mol). The mixture was heated to 90° C. and kept at this temperature for 18 h. After cooling to 20-25° C., methyl-tert-butyl ether was added (500 mL) and saturated aqueous NaHCO3 (250 mL). Some precipitation was removed by filtration and washed with 100 mL of methyl-tert-butyl ether. The filtrate was washed with 200 mL of saturated aqueous NaHCO3. After drying over Na2SO4, the organic phase was concentrated to give 2-((4R,6S)-2,2-dimethyl-6-((1-methyl-1H-tetrazol-5-ylthio)methyl)-1,3-dioxan-4-yl)acetic acid methyl ester as a solid (Compound C, 45.2 g, yield 71%). 1H NMR (300 MHz, CDCl3) δ 4.40-4.22 (m, 2H), 3.92 (s, 3H), 3.68 (s, 3H), 3.40 (dd, 2H), 2.48 (dd, 2H), 1.74 (dt, 1H), 1.42 (s, 3H), 1.39-1.29 (m, 1H), 1.35 (s, 3H).

Provenance & Evidence