676596-53-5

Basic information

• Product Name: L-Proline, 1-acetyl-4-(phenylmethoxy)-, methyl ester, (4R)-
• CAS NO: 676596-53-5
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.32
• Mol File: 676596-53-5.mol

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-acetyl-4-(phenylmethoxy)-, methyl ester, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-acetyl-4-(phenylmethoxy)-, methyl ester, (4R)-(676596-53-5)
• EPA Substance Registry System: L-Proline, 1-acetyl-4-(phenylmethoxy)-, methyl ester, (4R)-(676596-53-5)

Safety Data

• Hazardous Substances Data: 676596-53-5(Hazardous Substances Data)

Upstream product

• 113490-76-9 4(R)-(phenylmethoxy)-(S)-proline methyl ester 
• 75-36-5 acetyl chloride 
• 66831-17-2 (2S,4R)-methyl 4-(benzyloxy)pyrrolidine-2-carboxylate hydrochloride 

Downstream Products

• 287182-89-2 (2S,4R)-1-acetyl-N-[(1S)-1-(2-benzothiazolylhydroxymethyl)-4-[[imino[[(4-methylphenyl)sulfonyl]amino]methyl]amino]butyl]-4-(phenylmethoxy)-2-pyrrolidinecarboxamide 
• 182964-78-9 trans-1-acetyl-4-benzyloxy-L-proline 

Relevant articles and documents

Process for preparing peptidyl heterocyclic ketone derivatives

The present invention relates to novel processes for the preparation of peptidyl heterocyclic ketones of the general formula (I) wherein all variables are as herein defined. The present invention further relates to novel pharmaceutical salts and processes

Potent, small-molecule inhibitors of human mast cell tryptase. Antiasthmatic action of a dipeptide-based transition-state analogue containing a benzothiazole ketone

Inhibitors of human mast cell tryptase (EC 3.4.21.59) have therapeutic potential for treating allergic or inflammatory disorders. We have investigated transition-state mimetics possessing a heterocycle-activated ketone group and identified in particular benzothiazole ketone (2S)-6 (RWJ-56423) as a potent, reversible, low-molecular-weight tryptase inhibitor with a Ki value of 10 nM. A single-crystal X-ray analysis of the sulfate salt of (2S)-6 confirmed the stereochemistry. Analogues 12 and 15-17 are also potent tryptase inhibitors. Although RWJ-56423 potently inhibits trypsin (Ki = 8.1 nM), it is selective vs other serine proteases, such as kallikrein, plasmin, and thrombin. We obtained an X-ray structure of (2S)-6 complexed with bovine trypsin (1.9-? resolution), which depicts inter alia a hemiketal involving Ser-189, and hydrogen bonds with His-57 and Gln-192. Aerosol administration of 6 (2R,2S; RWJ-58643) to allergic sheep effectively antagonized antigen-induced asthmatic responses, with 70-75% blockade of the early response and complete ablation of the late response and airway hyperresponsiveness.

O-benzyl hydroxyproline as a bioisostere for Phe-Pro: Novel dipeptide thrombin inhibitors

A series of analogs were prepared based on the known thrombin inhibitor PPACK, in which the D-Phe-Pro dipeptide has been replaced by trans-4-O-benzyl hydroxyproline. One of these analogs is a more potent inhibitor of thrombin, and is more selective, than PPACK itself.