Propionic Acid (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester

Base Information

• Chemical Name: Propionic Acid (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester
• CAS No.: 187324-67-0
• Molecular Formula: C28H33 N O4 S
• Molecular Weight: 479.64
• DSSTox Substance ID: DTXSID00449894
• Nikkaji Number: J1.170.403D
• Wikidata: Q82269432
• Mol file: 187324-67-0.mol

Synonyms:187324-67-0;Propionic Acid (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester;(1S,2R)-2-(N-Benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl propionate;[(1S,2R)-2-[benzyl-(2,4,6-trimethylphenyl)sulfonylamino]-1-phenylpropyl] propanoate;DTXSID00449894;WNCDSLPLRUHTTL-YIXXDRMTSA-N;MFCD02093491;(1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Propionate;P1372;J-012058;(1S,2R)-N-Benzyl-N-(mesitylenesulfonyl)-O-propionylnorephedrine;Propanoic acid (1S,2R)-1-phenyl-2-(benzylmesitylsulfonylamino)propyl ester;(1S,2R)-2-[Benzyl(2,4,6-trimethylbenzene-1-sulfonyl)amino]-1-phenylpropyl propanoate;Propionic acid (1S2R)-2-[n-benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl ester;Propionic acid(1s2r)-2-[n-benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl ester

Chemical Property of Propionic Acid (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 149 °C
• Refractive Index: 1.579
• Boiling Point: 615.161°C at 760 mmHg
• Flash Point: 325.838°C
• PSA: 72.06000
• Density: 1.163g/cm³
• LogP: 6.96650
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 479.21302971
• Heavy Atom Count: 34
• Complexity: 724

Purity/Quality:

98% ^*data from raw suppliers

[(1S,2R)-2-[benzyl-(2,4,6-trimethylphenyl)sulfonylamino]-1-phenylpropyl]propanoate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OC(C1=CC=CC=C1)C(C)N(CC2=CC=CC=C2)S(=O)(=O)C3=C(C=C(C=C3C)C)C
• Isomeric SMILES: CCC(=O)O[C@@H](C1=CC=CC=C1)[C@@H](C)N(CC2=CC=CC=C2)S(=O)(=O)C3=C(C=C(C=C3C)C)C

Technology Process of Propionic Acid (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl Ester

There total 5 articles about Propionic Acid (1S,2R)-2-[N-Benzyl-N-(mesitylenesulfonyl)amino]-1-phenylpropyl 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: 100.0%

propionyl chloride (79-03-8) + (1S,2R)-2-[N-benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol (187324-64-7) → (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate (187324-67-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ja963754f

Reference yield:

(1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) → (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate (187324-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 95 percent / potassium carbonate / acetonitrile / 7 h / Heating

3: 100 percent / pyridine / CH₂Cl₂ / 13 h / 20 °C

With pyridine; potassium carbonate; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1021/jo0257896

Reference yield:

(1S,2R)-2-(N-mesitylenesulfonylamino)-1-phenylpropan-1-ol (187324-62-5) → (1S,2R)-2-(N-benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl propionate (187324-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / potassium carbonate / acetonitrile / 7 h / Heating

2: 100 percent / pyridine / CH₂Cl₂ / 13 h / 20 °C

With pyridine; potassium carbonate; In dichloromethane; acetonitrile;

DOI:10.1021/jo0257896

upstream raw materials:

propionyl chloride

(1S,2R)-2-[N-benzyl-N-(mesitylenesulfonyl)amino]-1-phenyl-1-propanol

2-mesitylenesulphonyl chloride

(1S,2R)-(+)-norphedrine

Downstream raw materials:

(2S,3S,4S,E)-((1S,2R)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-7-iodo-2,4,6-trimethylhept-6-enoate

C₄₂H₆₁NO₅S

C₄₃H₄₆BrNO₇S

cyclohexanol

Refernces

• 1、 Chen, Tao,Altmann, Karl-Heinz. "Directed hydrogenations and an Ireland-Claisen rearrangement linked to Evans-Tishchenko chemistry: The highly efficient total synthesis of the marine cyclodepsipeptide doliculide". supporting information. p. 8403 - 8407. Retrieved 2015/06/02.
• 2、 Abiko,Liu,Masamune. "The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters". . p. 2586 - 2587. Retrieved 2007/10/03.