Nateglinide

The above information is edited by the chemicalbook of Tian Ye.Nateglinide and mitiglinide, repaglinide are three commonly used non-sulfonylurea oral hypoglycemic agents for insulin secretion,it is successfully developed for the first time by the Japanese company Ajomoto , its chemical structure belongs to carbamoylmethyl-benzoic acid (CMBA), it belongs to D-phenylalanine derivatives, it is a new generation of antidiabetic drugs having amino acid structure ,it is an amino acid derivati

(2S)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic acid is a phenylalanine derivative.

Preparation of Nateglinide Form δ Hydrolysis of Methyl ester of Nateglinide; Methanol (1500 mL) and methyl ester of nateglinide (200 g) (as described in example 2) were taken in round bottom flask at 25-3OPreparation of Nateglinide; Methylene chloride (6000 mL), trans-4-isopropylcyclohexane (200 g) followed by para toluene sulfonyl chloride (208.38 g) and triethyl amine (409 mL) were added in a round bottom flask at 25-3OCondensation reaction:36 g of sodium hydroxide solid particles were dissolved in 960 g of deionized water, After dissolving, 366 g of acetone was added, Forming a mixed solution, The mixture was then cooled to 0 ° C with ice brine, Then, 60 g of D-phenylalanine was added, Stir until completely dissolved, Adding 60 g of the chlorination solution prepared in the previous step, Precipitation of a large number of white floc, Keep the temperature of 20 water bath will rise in the white floc dissolved, Keep 20 water bath reaction 20h, The pH of the reaction solution after 20 hours of reaction was adjusted to 3 with 150 g of hydrochloric acid having a mass fraction of 50percentAnd then in 20 water bath conditions for 10h, The resulting reaction product was then suction filtered, the cake was filtered, and the filter cake was washed with deionized water to give 80 g of crude nateglinide.Refined: 80g crude dissolved in 400g of 95percent ethanol, 78 reflux 0.5h after the filter, take the filtrate, add the filtrate to add 700g of dehydrated water, the filtrate becomes turbid, when the filtrate temperature dropped to 52 when added 0.4g nateglinide seed crystals, the crystal after the emergence of 28 water bath to 27 after the filter, filter cake, washed with deionized water and then placed in a vacuum drying oven 90 drying 10h, 70g white powder , The yield was 116.7percent.The purity of nateglinide measured by high performance liquid chromatography was 99.95percent. Nateglinide impurity0.02percent, nateglinide impurity b = 0.01percent, nateglinide impurity c = 0.01percent, nateglinide impurity d = 0.01percentAmerican Standard USP34.

An Amino-acid derivative that stimulates insulin secretion.Used as an antidiabetic

Molecular Weight:317.4
XLogP3:3.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:317.19909372
Monoisotopic Mass:317.19909372
Topological Polar Surface Area:66.4
Heavy Atom Count:23
Complexity:393
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes