(R)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid ethyl ester

Base Information

• Chemical Name: (R)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid ethyl ester
• CAS No.: 147770-08-9
• Molecular Formula: C29H40N2O4
• Molecular Weight: 480.648
• Mol file: 147770-08-9.mol

Synonyms:(R)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid ethyl ester;2-Ethoxy-4-[2-[[(1R)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid ethyl ester;(R)-Repaglinide Ethyl Ester;Repaglinide iMpurity (R-Repaglinide Ethyl Ester)

Chemical Property of (R)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid ethyl ester

Chemical Property:

• Melting Point: 122-124℃
• Boiling Point: 664.1±55.0 °C(Predicted)
• PKA: 14.79±0.46(Predicted)
• PSA: 67.87000
• Density: 1.093
• LogP: 6.15430

Purity/Quality:

99% ^*data from raw suppliers

(R)-RepaglinideEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid ethyl ester is an impurity of Repaglinide (R144500), a non-sulfonylurea oral hypoglycemic agent used as an antidiabetic. (R)-Repaglinide Ethyl Ester is an impurity of Repaglinide (R144500), a non-sulfonylurea oral hypoglycemic agent used as an antidiabetic.

Technology Process of (R)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid ethyl ester

There total 28 articles about (R)-2-Ethoxy-4-[2-[[3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid 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: 69.0%

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid (99469-99-5) + (R)-3-Methyl-1-(2-piperidin-1-yl-phenyl)-butylamine; compound with pentanedioic acid → (R)-(-)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate (147770-08-9)

Guidance literature:

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

DOI:10.1021/jm9810349

Reference yield:

2-(piperidin-1-yl)benzonitrile (72752-52-4) → (R)-(-)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate (147770-08-9)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran; toluene / 3 h / Heating

2: 34 percent / toluene / 15 h / Ambient temperature

3: H₂, NaOH, Et₃N, Ti(OiPr)4 / Ru(OAc)2<(S)-BINAP> / methanol; CH₂Cl₂ / 170 h / 30 °C / 75006 Torr

4: aq. HCl / 5.5 h / Heating

5: 19 percent / PPh₃, Et₃N, CCl₄ / acetonitrile / 15 h / Ambient temperature

With titanium(IV) isopropylate; hydrogenchloride; tetrachloromethane; sodium hydroxide; hydrogen; triethylamine; triphenylphosphine; Ru(OCOCH₃)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jm9810349

Reference yield:

piperidine (110-89-4) → (R)-(-)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate (147770-08-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / N-formyl-piperidine / 64 h / 160 - 170 °C

2: tetrahydrofuran; toluene / 3 h / Heating

3: 34 percent / toluene / 15 h / Ambient temperature

4: H₂, NaOH, Et₃N, Ti(OiPr)4 / Ru(OAc)2<(S)-BINAP> / methanol; CH₂Cl₂ / 170 h / 30 °C / 75006 Torr

5: aq. HCl / 5.5 h / Heating

6: 19 percent / PPh₃, Et₃N, CCl₄ / acetonitrile / 15 h / Ambient temperature

With N-Formylpiperidine; titanium(IV) isopropylate; hydrogenchloride; tetrachloromethane; sodium hydroxide; hydrogen; triethylamine; triphenylphosphine; Ru(OCOCH₃)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jm9810349

upstream raw materials:

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

(R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine

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

piperidine

Refernces