In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 25662-28-6 as follows. Safety of Methyl 1-cyclopentene-1-carboxylate
EXAMPLE 37; N-((lR)-l-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}ethyl)-2- fluoro- 1 -hydroxy cyclopentanecarboxamide; Methyl cyclopent-1-ene-l-carboxylate (30.0 g, 237.8 mmol) was dissolved in 20 mL of dichloromethane and 3-chloroperbenzoic acid (64.4 g, 373.3 mmol) was added. The reaction was allowed to stir vigorously for 2 hours. The reaction mixture was diluted with EtOAc and washed with 0.5 NNuaOEta. The organic layer was dried over sodium sulfate, filtered and concentrated to give 48.0 grams of methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate. Methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate (2.10 g, 14.8 mmol) and N,N-diethyl- ethanamine trihydrofluoride (4.76 g, 29.5 mmol) were heated in a sealable Emrys microwave vessel with stir bar a microwave reactor at 180 0C for 30 minutes. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was further washed with water and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated to a crude oil, which was subjected to chromatography on silica gel eluting with 0 to 25% EtOAc in hexanes to afford racemic trans methyl^-fluoro-l-hydroxycyclopentanecarboxylate.The racemic trans methyl-2-fluoro-l-hydroxycyclopentanecarboxylate (0.285 g, 1.76 mmol) was dissolved in 21.3 mL of a 4:1 solution of TEtaF:deionized water. A solution of 1 NNaOH was added to the reaction mixture, which was stirred for 1.5 hours. The reaction was acidified with 6 NHCl and extracted with EtOAc three times. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid as a colorless oil.To a mixture of the compound of Reference Example 4 (0.215 g, 6.13 mmol), racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid (90.8 mg, 0.61 mmol), and (lH-l,2,3-benzotriazol- l-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (0.380 g, 0.86 mmol) in 3 mL of dichloromethane was added triethylamine (0.155 g, 1.53 mmol). This reaction mixture was allowed to stir at ambient temperature for 1 hour. The reaction mixture was washed with water, 0.25 NEtaC1, and EPO
According to the analysis of related databases, 25662-28-6, the application of this compound in the production field has become more and more popular.
Reference:
Patent; MERCK & CO., INC.; WO2006/132837; (2006); A1;,
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