(2S)-1-[(S)-2-Phthalimidyl-3-phenylpropanoyl]-1,2,3,4-tetrahydropyridine-2alpha-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S)-1-[(S)-2-Phthalimidyl-3-phenylpropanoyl]-1,2,3,4-tetrahydropyridine-2alpha-carboxylic acid methyl ester
• CAS No.: 111581-88-5
• Molecular Formula: C₂₄H₂₂N₂O₅
• Molecular Weight: 418.449
• European Community (EC) Number: 601-106-5
• DSSTox Substance ID: DTXSID201103782
• Nikkaji Number: J3.043.159F
• Mol file: 111581-88-5.mol

Synonyms:SCHEMBL8786468;DTXSID201103782;(2S)-1-[(S)-2-Phthalimidyl-3-phenylpropanoyl]-1,2,3,4-tetrahydropyridine-2alpha-carboxylic acid methyl ester;111581-88-5;Methyl (2S)-1-[(2S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylate

Chemical Property of (2S)-1-[(S)-2-Phthalimidyl-3-phenylpropanoyl]-1,2,3,4-tetrahydropyridine-2alpha-carboxylic acid methyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 418.15287181
• Heavy Atom Count: 31
• Complexity: 733

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1CCC=CN1C(=O)C(CC2=CC=CC=C2)N3C(=O)C4=CC=CC=C4C3=O
• Isomeric SMILES: COC(=O)[C@@H]1CCC=CN1C(=O)[C@H](CC2=CC=CC=C2)N3C(=O)C4=CC=CC=C4C3=O

Technology Process of (2S)-1-[(S)-2-Phthalimidyl-3-phenylpropanoyl]-1,2,3,4-tetrahydropyridine-2alpha-carboxylic acid methyl ester

There total 11 articles about (2S)-1-[(S)-2-Phthalimidyl-3-phenylpropanoyl]-1,2,3,4-tetrahydropyridine-2alpha-carboxylic acid 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: 93.0%

C26H30N2O7 (116330-74-6) → [S(R*,R*)]-1-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylicacid, methyl ester (111581-88-5)

Guidance literature:

With trifluoroacetic acid; In chloroform; for 72h; Reflux; Molecular sieve;

DOI:10.1021/jm801146d

Reference yield: 72.0%

(S)-2-[(S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-6-oxo-hexanoic acid methyl ester (142589-43-3) → [S(R*,R*)]-1-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylicacid, methyl ester (111581-88-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h; Reflux;

Reference yield:

phthaloyl-L-phenylalanyl chloride (32150-91-7) → [S(R*,R*)]-1-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,2,3,4-tetrahydro-2-pyridinecarboxylicacid, methyl ester (111581-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4-methyl-morpholine / acetonitrile; ethyl acetate / -10 °C / Large scale

1.2: 0 °C / Large scale

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -60 °C / Inert atmosphere; Cooling with acetone-dry ice

2.2: 0.17 h / 0 °C

3.1: magnesium sulfate; trifluoroacetic acid / 3 h / 20 - 25 °C / Inert atmosphere

With 4-methyl-morpholine; oxalyl dichloride; magnesium sulfate; dimethyl sulfoxide; trifluoroacetic acid; In dichloromethane; ethyl acetate; acetonitrile; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1021/op970125x

upstream raw materials:

(S)-2-[(S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-6-oxo-hexanoic acid methyl ester

C₂₆H₃₀N₂O₇

phthaloyl-L-phenylalanyl chloride

(S)-2-amino-6-hydroxyhexanoic acid

Downstream raw materials:

(4S,7S,12bR)-7-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-6-oxo-1,2,3,4,6,7,8,12b-octahydro-benzo[c]pyrido[1,2-a]azepine-4-carboxylic acid benzhydryl ester

(4S,7S,12bR)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-6-oxo-1,2,3,4,6,7,8,12b-octahydro-benzo[c]pyrido[1,2-a]azepine-4-carboxylic acid benzhydryl ester

(4S,7S,12bR)-7-Amino-6-oxo-1,2,3,4,6,7,8,12b-octahydro-benzo[c]pyrido[1,2-a]azepine-4-carboxylic acid benzhydryl ester