(1S)-2-Oxo-1-phenyl-2-[(phenylmethyl)amino]ethyl (alphaS,3aR,7aS)-octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoate

Base Information

• Chemical Name: (1S)-2-Oxo-1-phenyl-2-[(phenylmethyl)amino]ethyl (alphaS,3aR,7aS)-octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoate
• CAS No.: 197447-44-2
• Molecular Formula: C₃₄H₃₈N₂O₄
• Molecular Weight: 538.687
• DSSTox Substance ID: DTXSID001105499
• Nikkaji Number: J880.185A
• Mol file: 197447-44-2.mol

Synonyms:DTXSID001105499;(1S)-2-Oxo-1-phenyl-2-[(phenylmethyl)amino]ethyl (alphaS,3aR,7aS)-octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoate;(2S)-2-Benzyl-4-[[(3aR,7aS)-hexahydroisoindolin]-2-yl]-4-oxobutyric acid (S)-1-phenyl-2-oxo-2-(benzylamino)ethyl ester;197447-44-2

Chemical Property of (1S)-2-Oxo-1-phenyl-2-[(phenylmethyl)amino]ethyl (alphaS,3aR,7aS)-octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoate

Chemical Property:

• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 538.28315770
• Heavy Atom Count: 40
• Complexity: 814

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC2CN(CC2C1)C(=O)CC(CC3=CC=CC=C3)C(=O)OC(C4=CC=CC=C4)C(=O)NCC5=CC=CC=C5
• Isomeric SMILES: C1CC[C@H]2CN(C[C@H]2C1)C(=O)C[C@H](CC3=CC=CC=C3)C(=O)O[C@@H](C4=CC=CC=C4)C(=O)NCC5=CC=CC=C5

Technology Process of (1S)-2-Oxo-1-phenyl-2-[(phenylmethyl)amino]ethyl (alphaS,3aR,7aS)-octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoate

There total 4 articles about (1S)-2-Oxo-1-phenyl-2-[(phenylmethyl)amino]ethyl (alphaS,3aR,7aS)-octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoate 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: 45.3%

(S)-N-benzylmandelamide (82270-62-0) + 4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic acid (145324-18-1) → (S)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid (S)-benzylcarbamoyl-phenyl-methyl ester (197447-44-2) + (R)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid (S)-benzylcarbamoyl-phenyl-methyl ester

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; a) 0 deg C, 2 h, b) RT, overnight;

DOI:10.1248/cpb.45.1518

Reference yield:

cis-hexahydroisoindoline (1470-99-1,1220913-24-5) → (S)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid (S)-benzylcarbamoyl-phenyl-methyl ester (197447-44-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 74.9 percent / CH₂Cl₂ / a) 0 deg C, 2 h, b) RT, overnight

2: 90.6 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr

3: 39.1 percent / DCC, DMAP / CH₂Cl₂ / a) 0 deg C, 2 h, b) RT, overnight

With dmap; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1248/cpb.45.1518

Reference yield:

4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid (145323-82-6) → (S)-2-Benzyl-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid (S)-benzylcarbamoyl-phenyl-methyl ester (197447-44-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90.6 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr

2: 39.1 percent / DCC, DMAP / CH₂Cl₂ / a) 0 deg C, 2 h, b) RT, overnight

With dmap; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1248/cpb.45.1518

upstream raw materials:

(S)-N-benzylmandelamide

4-[(3aR,7aS)-octahydro-2H-isoindol-2-yl]-4-oxo-2-benzyl-butanoic acid

cis-hexahydroisoindoline

4-(3aR,7aS)-Octahydro-isoindol-2-yl-4-oxo-2-[1-phenyl-meth-(E)-ylidene]-butyric acid

Downstream raw materials:

mitiglinide