1. Introduction
3-(N-Tosyl-L-alaninyloxy)-5-Phenylpyrrole, a synthetic organic compound widely recognized in pharmaceutical intermediate research. With the CAS registry number 99740-00-8, it plays a key role in drug discovery and development, particularly in peptide chemistry and heterocyclic compound synthesis.
2. Chemical Identity
Chemical Name: 3-(N-Tosyl-L-alaninyloxy)-5-Phenylpyrrole
CAS Number: 99740-00-8
Molecular Formula: C20H20N2O4S
Molecular Weight: 384.45 g/mol
Synonyms:
3-(N-Tosyl-L-alaninyloxy)-5-phenyl-1H-pyrrole
N-Tosyl-L-alanyl ester of 5-phenylpyrrole-3-ol
3. Structural Features
The compound consists of a pyrrole ring substituted with a phenyl group at position 5 and an N-tosyl-L-alaninyloxy moiety at position 3.
Key structural advantages include:
Enhanced lipophilicity from the phenyl substituent.
Tosyl-protected amino acid ester group, which offers stability in synthetic routes.
Functional handles for further derivatization in medicinal chemistry.
4. Physical and Chemical Properties
| Property | Value / Description |
|---|---|
| Appearance | White to off-white crystalline powder |
| Purity | ≥98% (typical for research use) |
| Solubility | Soluble in common organic solvents (e.g., DCM, chloroform, ethanol) |
| Stability | Stable under standard storage conditions, protected from moisture and light |
| Storage | Store at 2–8°C in airtight containers |
5. Applications
5.1 Pharmaceutical Intermediates
This compound is commonly used as a building block in the synthesis of bioactive molecules, particularly:
Peptide-based drugs – as a protected amino acid derivative.
Heterocyclic compounds – core unit for pyrrole-containing drug candidates.
Enzyme inhibitors – structural motifs suitable for binding in active sites.
5.2 Research in Medicinal Chemistry
Lead compound development for anti-inflammatory, antimicrobial, and anticancer agents.
SAR (Structure-Activity Relationship) studies to optimize pharmacokinetic properties.
6. Synthesis Overview
A general synthetic approach involves:
Preparation of 5-phenylpyrrole-3-ol as the core heterocycle.
Esterification with N-tosyl-L-alanine using coupling agents such as DCC or EDCI.
Purification via column chromatography to achieve high-purity material.
7. Handling and Safety
Hazard classification: Not classified as hazardous under GHS, but laboratory precautions apply.
Protective measures: Use gloves, goggles, and operate under a fume hood.
Waste disposal: Follow local regulations for organic chemical disposal.
8. Global Market and Supply
Demand for 3-(N-Tosyl-L-alaninyloxy)-5-Phenylpyrrole is driven by pharmaceutical R&D, especially in peptide synthesis.
Key supply regions include China, India, and Europe, where specialized chemical manufacturers offer both small-scale lab quantities and bulk production.
9. How to Choose a Reliable Supplier
When sourcing this compound:
Check COA and MSDS for quality confirmation.
Ensure batch-to-batch consistency for reproducible results.
Look for custom synthesis services if derivatives or isotopically labeled versions are required.
10. Conclusion
3-(N-Tosyl-L-alaninyloxy)-5-Phenylpyrrole (CAS 99740-00-8) is an important intermediate in modern medicinal chemistry, valued for its structural versatility and stability. With growing interest in pyrrole-based drug discovery, its role in research and industrial synthesis is expected to expand.