Nateglinide Methyl Ester

Base Information

• Chemical Name: Nateglinide Methyl Ester
• CAS No.: 105746-47-2
• Molecular Formula: C20H29NO3
• Molecular Weight: 331.455
• DSSTox Substance ID: DTXSID201141916
• Mol file: 105746-47-2.mol

Synonyms:Nateglinide Methyl Ester;105746-47-2;methyl (2R)-3-phenyl-2-[(4-propan-2-ylcyclohexanecarbonyl)amino]propanoate;NATEGLINIDE IMPURITY 7;NATEGLINIDEIMPURITY7;SCHEMBL1692380;SCHEMBL3712356;methyl (2R)-3-phenyl-2-{[4-(propan-2-yl)cyclohexyl]formamido}propanoate;SCHEMBL14357888;D-Phenylalanine, N-[[cis-4-(1-methylethyl)cyclohexyl]carbonyl]-, methyl ester;LUSNEIVFFXOKHW-KZNAEPCWSA-N;DTXSID201141916;958230-60-9;N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine methyl ester;N-(trans-4 isopropyl-cyclohexyl carbonyl)-D-Phenyl alanine methyl ester;D-Phenylalanine, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-, methyl ester;n-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]-d-phenylalanine methyl ester;N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-D-phenylalanine methyl ester;D-Phenylalanine, N-[[4-(1-methylethyl)cyclohexyl]carbonyl]-, methyl ester, trans-

Chemical Property of Nateglinide Methyl Ester

Chemical Property:

• PSA: 55.40000
• LogP: 3.74020
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 331.21474379
• Heavy Atom Count: 24
• Complexity: 407

Purity/Quality:

99.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CCC(CC1)C(=O)NC(CC2=CC=CC=C2)C(=O)OC
• Isomeric SMILES: CC(C)C1CCC(CC1)C(=O)N[C@H](CC2=CC=CC=C2)C(=O)OC

Technology Process of Nateglinide Methyl Ester

There total 9 articles about Nateglinide Methyl Ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methanol (67-56-1) + nateglinide (105816-04-4,105816-05-5) → N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester (105746-47-2)

Guidance literature:

With sulfuric acid; Reflux;

DOI:10.1016/j.chempr.2018.09.027

Reference yield: 90.07%

trans-4-isopropylcyclohexane-1-carboxylic acid (7077-05-6) + D-phenylalanine methyl ester hydrochloride (13033-84-6) → N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester (105746-47-2)

Guidance literature:

trans-4-isopropylcyclohexane-1-carboxylic acid; With pivaloyl chloride; triethylamine; In acetone; at 0 - 25 ℃; for 3.5h;

D-phenylalanine methyl ester hydrochloride; With triethylamine; In acetone; at 15 - 25 ℃; Product distribution / selectivity;

Reference yield:

methanol (67-56-1) + trans-4-isopropylcyclohexane-1-carboxylic acid (7077-05-6) + D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester (105746-47-2)

Guidance literature:

methanol; D-(R)-phenylalanine; With thionyl chloride; at 5 - 25 ℃; for 12.5h; Inert atmosphere;

With benzotriazol-1-ol; In dichloromethane; at 25 ℃; for 0.25h; Inert atmosphere;

trans-4-isopropylcyclohexane-1-carboxylic acid; With dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 15 ℃; for 3.25h;

upstream raw materials:

trans-4-isopropylcyclohexane-1-carboxylic acid

D-phenylalanine methyl ester

p-menthan-7-oic acid methyl ester

D-phenylalanine methyl ester hydrochloride

Downstream raw materials:

C₁₉H₂₆NO₃^(1-)*Na⁽¹⁺⁾

C₁₉H₂₆NO₃^(1-)*K⁽¹⁺⁾

nateglinide

Refernces

• 1、 Zhao, Da,Xu, Peng,Ritter, Tobias. "Palladium-Catalyzed Late-Stage Direct Arene Cyanation". supporting information. p. 97 - 107. Retrieved 2019/01/21.
• 2、 -. "A PROCESS FOR THE PREPARATION OF N-[[TRANS-4-(1-METHYLETHYL)CYCLOHEXYL]CARBONYL]-D-PHENYLALANINE". Page/Page column 17. . Retrieved 2010/10/03.