N-[2-[2-(4-Fluorophenyl)ethyl]-5-[[[(2S,4S)-4-[(3-pyridinylcarbonyl)thio]-2-pyrrolidinyl]methyl]amino]benzoyl]-L-methionine 1-methylethyl ester

Base Information

• Chemical Name: N-[2-[2-(4-Fluorophenyl)ethyl]-5-[[[(2S,4S)-4-[(3-pyridinylcarbonyl)thio]-2-pyrrolidinyl]methyl]amino]benzoyl]-L-methionine 1-methylethyl ester
• CAS No.: 345915-10-8
• Molecular Formula: C34H41FN4O4S2
• Molecular Weight: 652.854
• UNII: F99W9H5WUE
• ChEMBL ID: CHEMBL53670
• Nikkaji Number: J2.609.573E
• Mol file: 345915-10-8.mol

Synonyms:345915-10-8;AZD-3409;epi-921;UNII-F99W9H5WUE;F99W9H5WUE;CHEMBL53670;AZD 3409;N-[2-[2-(4-FLUOROPHENYL)ETHYL]-5-[[[(2S,4S)-4-[(3-PYRIDINYLCARBONYL)THIO]-2-PYRROLIDINYL]METHYL]AMINO]BENZOYL]-L-METHIONINE 1-METHYLETHYL ESTER;(S)-isopropyl 2-(2-(4-fluorophenethyl)-5-((((2S,4S)-4-(nicotinoylthio)pyrrolidin-2-yl)methyl)amino)benzamido)-4-(methylthio)butanoate;Isopropyl (2S)-2-((2-(2-(4-fluorophenyl)ethyl)-5-(((2S,4S)-4-(pyridine-3-carbonylsulfanyl)pyrrolidin-2-yl)methylamino)benzoyl)amino)-4-methylsulfanyl-butanoate;L-Methionine, N-(2-(2-(4-fluorophenyl)ethyl)-5-((((2S,4S)-4-((3-pyridinylcarbonyl)thio)-2-pyrrolidinyl)methyl)amino)benzoyl)-, 1-methylethyl ester;N-(2-(2-(4-Fluorophenyl)ethyl)-5-((((2S,4S)-4-((3-pyridinylcarbonyl)thio)-2-pyrrolidinyl)methyl)amino)benzoyl)-L-methionine 1-methylethyl ester;propan-2-yl (2S)-2-[[2-[2-(4-fluorophenyl)ethyl]-5-[[(2S,4S)-4-(pyridine-3-carbonylsulfanyl)pyrrolidin-2-yl]methylamino]benzoyl]amino]-4-methylsulfanylbutanoate;SCHEMBL2365289;AMY16958;BDBM50143597;AC-31589;PD159798;(S)-2-(2-[2-(4-Fluoro-phenyl)-ethyl]-5-{[(1S,4S)-4-(pyridine-3-carbonylsulfanyl)-pyrrolidin-2-ylmethyl]-amino}-benzoylamino)-4-methylsulfanyl-butyric acid isopropyl ester

Chemical Property of N-[2-[2-(4-Fluorophenyl)ethyl]-5-[[[(2S,4S)-4-[(3-pyridinylcarbonyl)thio]-2-pyrrolidinyl]methyl]amino]benzoyl]-L-methionine 1-methylethyl ester

Chemical Property:

• Boiling Point: 783.8±60.0 °C(Predicted)
• PKA: 13.54±0.46(Predicted)
• PSA: 160.02000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 6.31770
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 17
• Exact Mass: 652.25532631
• Heavy Atom Count: 45
• Complexity: 938

Purity/Quality:

98%min ^*data from raw suppliers

AZD-3409 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)C(CCSC)NC(=O)C1=C(C=CC(=C1)NCC2CC(CN2)SC(=O)C3=CN=CC=C3)CCC4=CC=C(C=C4)F
• Isomeric SMILES: CC(C)OC(=O)[C@H](CCSC)NC(=O)C1=C(C=CC(=C1)NC[C@@H]2C[C@@H](CN2)SC(=O)C3=CN=CC=C3)CCC4=CC=C(C=C4)F

Technology Process of N-[2-[2-(4-Fluorophenyl)ethyl]-5-[[[(2S,4S)-4-[(3-pyridinylcarbonyl)thio]-2-pyrrolidinyl]methyl]amino]benzoyl]-L-methionine 1-methylethyl ester

There total 25 articles about N-[2-[2-(4-Fluorophenyl)ethyl]-5-[[[(2S,4S)-4-[(3-pyridinylcarbonyl)thio]-2-pyrrolidinyl]methyl]amino]benzoyl]-L-methionine 1-methylethyl 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: 79.0%

isopropyl N-{5-({[(2S,4S)-1-(tert-butoxycarbonyl)-4-(pyridin-3-ylcarbonyl)thiopyrrolidin-2-yl]methyl}amino)-2-[2-(4-fluorophenyl)ethyl]benzoyl}-L-methioninate (345915-09-5) → isopropyl N-{5-({[(2S,4S)-4-(pyridin-3-ylcarbonyl)thiopyrrolidin-2-yl]methyl}amino)-2-[2-(4-fluorophenyl)ethyl]benzoyl}-L-methioninate (345915-10-8)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; toluene; at 50 ℃; for 4h; Large scale;

DOI:10.1021/op700218j

Reference yield:

isopropyl N-{5-({[(2S,4S)-1-(tert-butoxycarbonyl)-4-(pyridin-3-ylcarbonyl)thiopyrrolidin-2-yl]methyl}amino)-2-[2-(4-fluorophenyl)ethyl]benzoyl}-L-methioninate (345915-09-5) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl N-{5-({[(2S,4S)-4-(pyridin-3-ylcarbonyl)thiopyrrolidin-2-yl]methyl}amino)-2-[2-(4-fluorophenyl)ethyl]benzoyl}-L-methioninate (345915-10-8) + tertiary butyl chloride (507-20-0) + isopropyl tert-butyl ether (17348-59-3)

Guidance literature:

With hydrogenchloride; In toluene; at 50 ℃; Concentration; Temperature; Kinetics; Inert atmosphere;

DOI:10.1021/jo101767h

Reference yield:

methyl 2-[(E)-2-(4-fluorophenyl)vinyl]-5-nitrobenzoate → isopropyl N-{5-({[(2S,4S)-4-(pyridin-3-ylcarbonyl)thiopyrrolidin-2-yl]methyl}amino)-2-[2-(4-fluorophenyl)ethyl]benzoyl}-L-methioninate (345915-10-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 2 h / 35 °C / Large scale

2.1: sodium hydroxide; methanol / 6.5 h / 60 °C / Large scale

3.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / water; 1-methyl-pyrrolidin-2-one / 10 h / 20 °C / Large scale

4.1: hydrogenchloride / toluene; isopropyl alcohol / 0.5 h / 20 °C / Large scale

4.2: 5.33 h / 20 °C / Large scale

5.1: toluene; isopropyl alcohol; acetonitrile / 4 h / 20 °C / Large scale

6.1: hydrogenchloride / toluene; isopropyl alcohol / 4 h / 50 °C / Large scale

With 4-methyl-morpholine; hydrogenchloride; methanol; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In 1-methyl-pyrrolidin-2-one; methanol; water; isopropyl alcohol; toluene; acetonitrile;

DOI:10.1021/op700218j

upstream raw materials:

isopropyl N-{5-({[(2S,4S)-1-(tert-butoxycarbonyl)-4-(pyridin-3-ylcarbonyl)thiopyrrolidin-2-yl]methyl}amino)-2-[2-(4-fluorophenyl)ethyl]benzoyl}-L-methioninate

isopropyl alcohol

2-chloro-5-nitro-benzoic acid methyl ester

para-fluorostyrene

Refernces

• 1、 Abbas, Sahar,Ferris, Leigh,Norton, Alison K.,Powell, Lyn,Robinson, Graham E.,Siedlecki, Paul,Southworth, Rebecca J.,Stark, Andrew,Williams, Emyr G.. "Application of an enantiomerically pure bicyclic thiolactone in the synthesis of a farnesyl transferase inhibitor". . p. 202 - 212. Retrieved 2013/01/03.