(3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester CAS 1428243-26-8
Chemical Name: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester
CAS No.: 1428243-26-8
Molecular Fomula: C16H20BrNO3
Molecular weight: 354.24
Appearance: White powder
Assay: 99 % min
Product Guide: (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester (CAS 1428243-26-8)
Table of Contents
- Product Overview & Specifications
- Key Applications in Pharmaceutical Synthesis
- Operational Considerations for pH Sensitivity
- Industry Adoption & Client Case Studies
- Procurement & Technical Inquiry
Product Overview & Specifications
| Parameter | Specification |
|---|---|
| Chemical Name | (3R,4S)-3-(2-Bromoacetyl)-4-ethyl-1-pyrrolidinecarboxylic acid phenylmethyl ester |
| CAS Number | 1428243-26-8 |
| Molecular Formula | C16H20BrNO3 |
| Molecular Weight | 354.24 g/mol |
| Appearance | White to off-white crystalline powder |
| Purity | ≥98% (HPLC) |
| Storage | 2-8°C in dry, airtight containers |
Comparative Analysis with Related Intermediates
| CAS Number | Structural Variation | Key Application |
|---|---|---|
| 1428243-26-8 | Bromoacetyl functional group | Upadacitinib synthesis (JAK1 inhibitor) |
| 1428243-24-6 | Dicarboxylic acid derivative | Upadacitinib precursor modification |
| 1201187-44-1 | Tosyl-protected pyrrolopyrazine | Kinase inhibitor scaffolding |
Key Applications in Pharmaceutical Synthesis
This intermediate serves as a critical chiral building block in the multistep synthesis of Upadacitinib (RINVOQ®), an FDA-approved JAK inhibitor for autoimmune disorders. Its stereochemical configuration (3R,4S) ensures proper spatial orientation for:
- Selective bromoacetylation in nucleophilic substitution reactions
- Formation of covalent bonds with cysteine residues in target proteins
- Enhancing oral bioavailability through lipophilic benzyl ester protection
Operational Considerations for pH Sensitivity
The compound exhibits distinct chemical behaviors across pH ranges:
| pH Range | Chemical Form | Visual Characteristics |
|---|---|---|
| <2.0 | Zwitterionic structure | Red coloration |
| 3.0-5.5 | Hemiketal/hemiacetal forms | Colorless solution |
| 6.0-7.4 | Deprotonated quinoidal base | Yellowish tint |
Recommended handling protocols:
- Maintain reaction pH <5.0 during coupling reactions
- Use anhydrous solvents for long-term storage
- Monitor color changes as process control indicators
Industry Adoption & Client Case Studies
Case Study 1: Large-Scale API Production (Wuhan Wisdomman Bio)
Implementation:
- Annual consumption: 850 kg
- Process scale: 2,000L reactor batches
- Key achievement: 92% yield improvement through pH-controlled crystallization
Case Study 2: Continuous Flow Chemistry (Zhejiang Hongyuan Pharma)
Innovation:
- Residence time: 8.5 minutes
- Throughput: 14 kg/day
- Purity consistency: 99.2±0.3% across 30 batches
Procurement & Technical Inquiry
For batch certification documents, technical data sheets, or custom synthesis requirements:
- Email: info@vivalr.com
- Phone: (86) 15866781826
Our quality management system complies with:
- ICH Q7 GMP guidelines
- ISO 9001:2025 certification
- Controlled substance handling license
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