Repaglinide ethyl ester

Base Information

• Chemical Name: Repaglinide ethyl ester
• CAS No.: 147770-06-7
• Molecular Formula: C29H40 N2 O4
• Molecular Weight: 480.648
• European Community (EC) Number: 604-604-0
• UNII: 3G7O9LRT91
• DSSTox Substance ID: DTXSID30163798
• Wikidata: Q27257171
• Mol file: 147770-06-7.mol

Synonyms:147770-06-7;Repaglinide ethyl ester;(S)-Ethyl 2-ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoate;(S)-Repaglinide Ethyl Ester (Repaglinide Impurity);(S)-Repaglinide ethyl ester;ethyl 2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoate;UNII-3G7O9LRT91;3G7O9LRT91;Repaglinide specified impurity D [EP];EC 604-604-0;(+)-Ethyl 2-ethoxy-4-(((N-(1-(2-piperidinophenyl)-3-methyl-1-butyl)amino)carbonyl)methyl)benzoate;(S)-Ethyl 2-ethoxy-4-(((N-(1-(2-piperidinophenyl)-3-methyl-1-butyl)amino)carbonyl)methyl)benzoate;Benzoic acid, 2-ethoxy-4-(2-(((1S)-3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)-, ethyl ester;Ethyl 2-ethoxy-4-(2-(((1S)-3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoate;(s)-2-ethoxy-4-(2-(3-methyl-1-(2-(piperidin-1-yl)phenyl)butylamino)-2-oxoethyl)benzoic acid ethyl ester;2-Ethoxy-4-(3-((S)-3-methy-1-(2-piperidin-1-yl-phenyl)-butylamino)-2-oxo-propyl)-benzoic acid ethyl ester;Benzoic acid, 2-ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]-, ethyl ester;Ethyl 2-Ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]amino]-2-oxoethyl]benzoate (Repaglinide Ethyl Ester);Repaglinide Impurity;2-Ethoxy-4-{3-[(S)-3-methy-1-(2-piperidin-1-yl-phenyl)-butylamino]-2-oxo-propyl}-benzoic acid ethyl ester;ethyl (S)-2-ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoate;ethyl (S)-2-ethoxy-4-[N-{1-(2-piperidinophenyl)-3-methyl-1-butyl}aminocarbonylmethyl]benzoate;SCHEMBL391046;DTXSID30163798;FTCMVLQJMIXDSI-VWLOTQADSA-N;MFCD12911752;AKOS015950800;DS-9696;CS-0151514;REPAGLINIDE IMPURITY D [EP IMPURITY];REPAGLINIDE ETHYL ESTER [USP IMPURITY];F52837;A884400;J-008409;Q27257171;(S)-Ethyl2-ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoate;BENZOIC ACID,2-ETHOXY-4-[2-[[(1S)-3-METHYL-1-[2-(1-PIPERIDINYL)PHENYL]BUTYL]AMINO]-2-OXOETHYL]-,ETHYL ESTER;ethyl (S)-2-ethoxy-4-(2-((3-methyl-1-(2-(piperidin-1-yl)phenyl)butyl)amino)-2-oxoethyl)benzoate;Ethyl (S)-2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-amino carbonylmethyl]-benzoate;Ethyl (S)-2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonyl methyl]-benzoate;Ethyl (S)-2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]-benzoate;Ethyl (S)-2-ethoxy-4-[N-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl]benzoate;ethyl (S)-2-ethoxy-4-[N-{1-(2-piperidinophenyl)-3-methyl-1-butyl}-aminocarbonylmethyl]benzoate;Ethyl(S)-2-ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonyl methyl]benzoate

Chemical Property of Repaglinide ethyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 115-118?C
• Boiling Point: 664.088°C at 760 mmHg
• PKA: 14.79±0.46(Predicted)
• Flash Point: 355.428°C
• PSA: 67.87000
• Density: 1.093±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 6.15430
• Storage Temp.: -20°C Freezer
• Solubility.: Chlorofrom, Methanol
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 480.29880776
• Heavy Atom Count: 35
• Complexity: 649

Purity/Quality:

99.9% ^*data from raw suppliers

(S)-RepaglinideEthylEster(RepaglinideImpurity) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=CC(=C1)CC(=O)NC(CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)OCC
• Isomeric SMILES: CCOC1=C(C=CC(=C1)CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)OCC
• Uses: Repaglinide impurity. Repaglinide impurity

Technology Process of Repaglinide ethyl ester

There total 47 articles about Repaglinide ethyl 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: 93.0%

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid (99469-99-5) + (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine (147769-93-5) → (S)-(+)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate (147770-06-7)

Guidance literature:

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid; With 1,1'-carbonyldiimidazole; In dichloromethane;

(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine; In dichloromethane; Product distribution / selectivity;

Reference yield: 59.0%

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid (99469-99-5) + regaliamine glutamate → (S)-(+)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate (147770-06-7)

Guidance literature:

With dicyclohexyl-carbodiimide; In toluene; for 2h; Ambient temperature;

DOI:10.1021/jm9810349

Reference yield:

2-(piperidin-1-yl)benzaldehyde (34595-26-1) → (S)-(+)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate (147770-06-7)

Guidance literature:

Multi-step reaction with 4 steps

1: Ambient temperature

2: Ti(OiPr)4 / tetrahydrofuran; toluene / 60 h / 100 °C

3: H₂, aq. HCl / 10 percent Pd/C / 5 h / 50 °C / 3750.3 Torr

4: 29 percent / PPh₃, Et₃N, CCl₄ / acetonitrile / 15 h / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; tetrachloromethane; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; toluene; acetonitrile;

DOI:10.1021/jm9810349

upstream raw materials:

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine

ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate

piperidine

Downstream raw materials:

(S)-repaglinide

Refernces

• 1、 -. "Synthesis method of repaglinide". Paragraph 0043; 0051; 0052. . Retrieved 2019/07/16.
• 2、 -. "Process for the preparation of substantially optically pure Repaglinide and precursors thereof". Page/Page column 13. . Retrieved 2010/05/13.