methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate

Base Information

• Chemical Name: methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate
• CAS No.: 1195787-88-2
• Molecular Formula: C₃₁H₃₀F₇N₃O₃
• Molecular Weight: 625.586
• Mol file: 1195787-88-2.mol

Synonyms:methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate

Chemical Property of methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate

There total 6 articles about methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate 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: 26.8%

methyl (2R)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-3,4-dihydro-2H-pyrrole-2-carboxylate (1195787-86-0) → methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate (1195787-88-2) + methyl (5R)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate (1195787-87-1)

Guidance literature:

methyl (2R)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-3,4-dihydro-2H-pyrrole-2-carboxylate; With borane-THF; In tetrahydrofuran; at -40 ℃;

With methanol; In tetrahydrofuran; at 20 ℃; for 2h; Product distribution / selectivity;

Reference yield:

(R)-2-aminopent-4-ynoic acid (23235-01-0,23235-03-2,50428-03-0,64165-64-6) → methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate (1195787-88-2) + methyl (5R)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate (1195787-87-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / 0 - 20 °C

2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 3 h / 20 °C

3.1: copper(l) iodide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine / bis-triphenylphosphine-palladium(II) chloride / 0.5 h / 100 °C / Microwave irradiation

4.1: trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice

4.2: 20 °C / pH 7

5.1: silver trifluoromethanesulfonate / acetonitrile / 20 °C

6.1: borane-THF / tetrahydrofuran / 2 h / -40 °C

6.2: 2 h / 20 °C

With copper(l) iodide; thionyl chloride; borane-THF; silver trifluoromethanesulfonate; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

Reference yield:

(R)-2-amino-4-pentynoic acid methyl ester (78342-50-4) → methyl (5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate (1195787-88-2) + methyl (5R)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-D-prolinate (1195787-87-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate / 1,4-dioxane; water / 3 h / 20 °C

2.1: copper(l) iodide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine / bis-triphenylphosphine-palladium(II) chloride / 0.5 h / 100 °C / Microwave irradiation

3.1: trifluoroacetic acid / dichloromethane / 20 °C / Cooling with ice

3.2: 20 °C / pH 7

4.1: silver trifluoromethanesulfonate / acetonitrile / 20 °C

5.1: borane-THF / tetrahydrofuran / 2 h / -40 °C

5.2: 2 h / 20 °C

With copper(l) iodide; borane-THF; silver trifluoromethanesulfonate; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetonitrile;

upstream raw materials:

methyl (2R)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-3,4-dihydro-2H-pyrrole-2-carboxylate

methyl (2R)-2-amino-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-4-pentynoate

methyl (2R)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-2-(([(1,1-dimethylethyl)oxy]carbonyl)amino)-4-pentynoate

(R)-2-aminopent-4-ynoic acid

Downstream raw materials:

1-(1,1-dimethylethyl) 2-methyl (2R,5S)-5-[5-[(2-[3,5-bis(trifluoromethyl)phenyl]-2-methylpropanoyl)(methyl)amino]-4-(4-fluoro-2-methylphenyl)-2-pyridinyl]-1,2-pyrrolidinedicarboxylate

Refernces

• 1、 -. "5-[5-[2-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-2-METHYLPROPANOYLMETHYLAMINO]-4-(4-FLUORO-2-METHYLPHENYL)]-2-PYRIDINYL-2-ALKYL-PROLINAMIDE AS NK1 RECEPTOR ANTAGONISTS". Page/Page column 46-47. . Retrieved 2009/12/23.