A common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 35180-01-9.
Example 1 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 1-[(isopropoxycarbonyl)oxy]methyl ester (compound 1) 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid (prepared by the method disclosed in U.S. Pat. No. 5,138,069) was reacted with trityl chloride to obtain 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid. To a 100 ml of one-necked flask, 0.523 g of 2-butyl-4-chloro-1-[2′-(1-triphenylmethyl-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 0.124 g of potassium carbonate, and 5 ml of N,N-dimethylacetamide were added in turn. The solution was stirred at the room temperature for 20 minutes. Then 0.562 g of 1-chloromethyl isopropyl carbonate was added and the mixture was reacted at 45-50 C. for 16 h. After the reaction was completed, the mixture solution was filtered, and 30 ml of water was added into the filtrate. The resulting mixture was extracted with 30 ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.724 g of oil, which was directly used in the next reaction without purification. 10 ml of dioxane and 5 ml of 4 mol/L HCl were added, and the resulting mixture was reacted at the room temperature for 16 h. After the reaction was completed, the solution was adjusted to pH 6-7 using aqueous sodium bicarbonate solution. The solution became turbid, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, concentrated to give 0.436 g of 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl]imidazole-5-carboxylic acid, 1-[(isopropoxycarbonyl)oxy]methyl ester. 1H-NMR: (CDCl3) deltaH (ppm): 0.89 (t, 3H, J=14.6), 1.24 (d, 6H, J=6.3), 1.37 (m, 2H, J=22.1), 1.69 (m, 2H, J=30.5), 2.64 (t, 2H, J=15.5), 4.81 (m, 1H, J=12.4), 5.54 (s, 2H), 5.86 (s, 2H), 6.95-7.64 (8H), 8.08 (d, 1H, J=7.42) ESI (+) m/z: 552.7
The synthetic route of Chloromethyl isopropyl carbonate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Guo, Jianhui; An, Dong; US2009/326024; (2009); A1;,
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