92010-20-3

Basic information

• Product Name: L-Proline, 1-benzoyl-, phenylmethyl ester
• CAS NO: 92010-20-3
• Molecular Formula: C19H19NO3
• Molecular Weight: 309.365
• Mol File: 92010-20-3.mol

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-benzoyl-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-benzoyl-, phenylmethyl ester(92010-20-3)
• EPA Substance Registry System: L-Proline, 1-benzoyl-, phenylmethyl ester(92010-20-3)

Safety Data

• Hazardous Substances Data: 92010-20-3(Hazardous Substances Data)

Upstream product

• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 41324-66-7 H-Pro-OBzl 

Downstream Products

• 83528-04-5 (S)-N-benzyl-O-benzylpyrrolidine-2-carboxylate 
• 69677-92-5 benzoyl-Pro-Phe-Arg 
• 88105-63-9 N-benzoyl-L-prolyl-L-phenylalanyl-N^ω-nitro-L-arginine methyl ester 
• 88105-64-0 N-benzoyl-L-prolyl-L-phenylalanyl-N^ω-nitro-L-arginine 
• 88130-47-6 N-benzoyl-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine methyl ester 
• 88130-48-7 N-benzoyl-L-prolyl-DL-α-methylphenylalanyl-N^ω-nitro-L-arginine 
• 88084-31-5 N-benzoyl-L-prolyl-DL-α-methylphenylalanyl-L-arginine 
• 88130-49-8 N-benzoyl-L-prolyl-DL-α-methylphenylalanyl-L-proline benzyl ester 
• 88084-33-7 N-benzoyl-L-prolyl-DL-α-methylphenylalanyl-L-proline 
• 88105-62-8 N-benzoyl-L-prolyl-L-phenylalanine benzyl ester 
• 88105-61-7 N-benzoyl-L-prolyl-DL-α-methylphenylalanine methyl ester 
• 59191-06-9 N-benzoyl-L-prolyl-L-phenylalanine 
• 88084-13-3 N-benzoyl-L-prolyl-DL-α-methylphenylalanine 
• 5874-58-8 N-(benzoyl)-L-proline 

Relevant articles and documents

Selective Rhodium-Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides

Efficient reduction of the tertiary amide bond in amino acid derivatives and peptides is described. Functional group selectivity has been achieved by applying a commercially available rhodium precursor and bis(diphenylphosphino)propane (dppp) ligand together with phenyl silane as a reductant. This methodology allows for specific reductive derivatization of biologically interesting peptides and offers straightforward access to a variety of novel peptide derivatives for chemical biology studies and potential pharmaceutical applications. The catalytic system tolerates a variety of functional groups including secondary amides, ester, nitrile, thiomethyl, and hydroxy groups. This convenient hydrosilylation reaction proceeds at ambient conditions and is operationally safe because no air-sensitive reagents or highly reactive metal hydrides are needed.

PS-IIDQ: a supported coupling reagent for efficient and general amide bond formation

Polystyrene-IIDQ, a polymer-supported coupling reagent, was synthesized in three steps from Merrifield resin in 86% overall conversion. This reagent efficiently coupled carboxylic acids to amines in good yields and high purities, required no pre-activation step, and was tolerant of the order of reagent addition. PS-IIDQ was observed to be more efficient than polymer-supported carbodiimides (PS-EDC and PS-DCC) and gave higher yields than HATU for general amide bond formation, including the coupling of anilines and hindered substrates. When evaluated with five carboxylic acids and nine amines (including anilines and secondary amines) PS-IIDQ gave an average isolated yield of 73%.

Efficient one-pot formation of amides from benzyl carbamates: Application to solid-phase synthesis

A convenient one-pot protocol for the conversion of benzyl carbamates to amides is described. The general applicability of the procedure is illustrated using various types of substrates. This new method proceeds rapidly under mild conditions, in good yields, and without noticeable racemization. This protocol was applied to solid-phase synthesis to prepare amides and esters from Merrifield resin-bound carbamates and carbonates. (C) 2000 Elsevier Science Ltd.

Lewis acid-catalyzed cleavage of carbamate and carbonate resins

A procedure for the preparation of amides and esters on a Merrifield resin-bound benzyloxycarbonyl equivalent has been developed. Polymer-supported carbamates react cleanly with zinc bromide and the appropriate acyl halide in the presence of triethylamine to provide their corresponding amides in high yields and purities. Cleavage of resin-bound carbonates was carried out using the similar reagent systems in the absence of triethylamine to give acetates or benzoates. (C) 2000 Elsevier Science Ltd.

Electronic effect of prolinate ligand-dirhodium(ii) complexes on catalytic asymmetric dipolar cycloaddition

We prepared several efficient chiral N-benzoylpyrroridinecarboxylic acid ligands for dirhodium-catalyzed asymmetric dipolar cycloaddition and found that the electronic effect of the dirhodium(II) complexes influenced the catalytic activity, and the electr

Steric and electronic effects of substrates and rhodium chiral catalysts in asymmetric cyclopropanation

We have prepared several new, efficient, chiral N-acyl pyrrolidine carboxylic acid ligands for dirhodium-catalyzed asymmetric cyclopropanation and found that the steric and electronic effects of the rhodium(II) complexes and substrates influenced the enan

Design, synthesis, and testing of potential antisickling agents. 5. Disubstituted benzoic acids designed for the donor site and proline salicylates designed for the acceptor site

This paper reports the discovery of a new class of potent antigelling agents. The new compounds, disubstituted benzoic acid derivatives, were designed by using molecular modeling experiments. These molecules contain functional groups positioned to interac

Tri- and tetrapeptide analogues of kinins as potential renal vasodilators

Tri- and tetrapeptide analogues were synthesized and evaluated as renal vasodilators. These peptides were prepared by standard coupling reactions which also provided good yields with hindered α-methyl amino acid derivatives. Preliminary evidence of renal vasodilator activity was determined in anesthetized dogs by measuring the effects on renal blood flow and calculating the accompanying changes in renal vascular resistance. The most potent compounds contained, in their structure, the L-prolyl-DL-α-methylphenylalanyl-L-arginine and L-prolyl-DL-α-methyl-phenyalanylglycyl-L-proline arrays. Substitution on the N-terminal proline with 4-phenylbutyryl and 4-(4-hydroxyphenyl)butyryl side chains produced enhanced renal vasodilator activity and, in certain cases, selectivity for the renal vasculature.