N-(4-Methoxybenzoyl)-L-proline

Base Information

• Chemical Name: N-(4-Methoxybenzoyl)-L-proline
• CAS No.: 62522-92-3
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90358704
• Nikkaji Number: J1.192.475A
• Wikidata: Q82139481
• Mol file: 62522-92-3.mol

Synonyms:N-(4-Methoxybenzoyl)-L-proline;62522-92-3;(2S)-1-(4-methoxybenzoyl)pyrrolidine-2-carboxylic acid;(S)-1-(4-Methoxybenzoyl)pyrrolidine-2-carboxylic acid;1-(4-METHOXYBENZOYL)PROLINE;1-(4-Methoxybenzoyl)-L-proline;SCHEMBL4001868;DTXSID90358704;MFCD09757467;AKOS010373057;AKOS015851951

Chemical Property of N-(4-Methoxybenzoyl)-L-proline

Chemical Property:

• Vapor Pressure: 6.27E-10mmHg at 25°C
• Refractive Index: 1.582
• Boiling Point: 477.6°C at 760 mmHg
• PKA: 5.37±0.10(Predicted)
• Flash Point: 242.6°C
• PSA: 66.84000
• Density: 1.291g/cm³
• LogP: 1.32230
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 323

Purity/Quality:

99% ^*data from raw suppliers

1-(4-Methoxybenzoyl)proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C(=O)N2CCCC2C(=O)O
• Isomeric SMILES: COC1=CC=C(C=C1)C(=O)N2CCC[C@H]2C(=O)O

Technology Process of N-(4-Methoxybenzoyl)-L-proline

There total 6 articles about N-(4-Methoxybenzoyl)-L-proline 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: 94.0%

H-Pro-2-chlorotritylchloride-resin + para-iodoanisole (696-62-8) + diphenylmethylsilanecarboxylic acid (18414-58-9) → (4-methoxybenzoyl)-L-proline (62522-92-3)

Guidance literature:

H-Pro-2-chlorotritylchloride-resin; para-iodoanisole; diphenylmethylsilanecarboxylic acid; With potassium fluoride; C₃₉H₃₂OP₂*C₁₃H₁₂N^(1-)*Pd⁽²⁺⁾*CH₃O₃S^(1-); triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 15h; wang polystyrene resin Sealed tube; Inert atmosphere;

With triethylsilane; trifluoroacetic acid; In water; at 20 ℃; for 2h; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01068

Reference yield: 69.0%

(4S)-1-(4'-methoxybenzoyl)-L-proline benzyl ester (174465-22-6) → (4-methoxybenzoyl)-L-proline (62522-92-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 16h; under 760 Torr;

DOI:10.1248/cpb.43.2048

Reference yield:

H-Pro-2-chlorotritylchloride-resin + 4-methoxybenzoic acid (100-09-4) → (4-methoxybenzoyl)-L-proline (62522-92-3)

Guidance literature:

H-Pro-2-chlorotritylchloride-resin; 4-methoxybenzoic acid; With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; wang polystyrene resin Inert atmosphere;

With triethylsilane; trifluoroacetic acid; In water; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01068

upstream raw materials:

(4S)-1-(4'-methoxybenzoyl)-L-proline benzyl ester

4-methoxy-benzoyl chloride

H-Pro-OBzl

para-iodoanisole

Downstream raw materials:

3-[2-(4-methoxyphenyl)-5-trifluoromethyloxazol-4-yl]propanol

((S)-2-{[(S)-1-(4-Methoxy-benzoyl)-pyrrolidine-2-carbonyl]-amino}-4-methyl-pentylsulfanyl)-acetic acid tert-butyl ester

Refernces

• 1、 Ishitani, Hitoshi,Achiwa, Kazuo. "Electronic effect of prolinate ligand-dirhodium(ii) complexes on catalytic asymmetric dipolar cycloaddition". . p. 153 - 156. Retrieved 2007/10/03.