(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
相关产品
Chemical Name: 4-((2-Furylmethyl)thio)-4-methylpentan-2-one
Cas No.: 64835-96-7
Molecular Fomula: C11H16O2S
Molecular Weight: 212.31
Appearance: Colorless to light yellow liquid
Chemical Name: D-PANTOTHENIC ACID
CAS No.: 79-83-4
Molecular Formula: C9H17NO5
Molecular Weight: 219.24
Appearance: Colorless or Light Yellow Oily Liquid
Chemical Name: 1,1,2,2-Tetrachloroethane
Other Name: Tetrachlorethane
CAS No.: 79-34-5
Molecular Formula: C2H2Cl4
Molecular Weight: 167.85
Appearance: Liquid
Chemical Name: Oxirane, methyl-, polymer with oxirane, dodecyl ether
Cas No.: 68238-81-3
Molecular Fomula: C17H36O3
Molecular Weight: 288.46594
Chemical Name: Zinc citrate
Synonyms: Zinc citrate trihydrate
CAS No.: 546-46-3
Molecular Formula: C6H8O7Zn
Molecular Weight: 257.5
Appearance: White powder
Chemical Name: Ethyl Hexanoate
Synonyms: Ethyl caproate; Caproic acid ethyl ester; Ethyl butyl acetate; capronic ether; hexanoic acid ethyl ester
CAS No.: 123-66-0
Molecular Formula: C8H16O2
Molecular Weight: 144.21
Chemical Name: Dehydrocholic acid
Synonyms: Acide dehydrocholique; Triketocholanic acid
CAS No.: 81-23-2
Molecular Formula: C24H34O5
Molecular Weight: 402.53
Appearance: Powder
Chemical Name: 1-Hexadecylamine
Synonyms 1-Aminohexadecane; Hexyldecylamine; n-Certylamine
CAS No.: 143-27-1
Molecular Formula: C16H35N
Molecular Weight: 241.46
Appearance: White Crystal
Chemical Name: D-Phenothrin
CAS No.: 26046-85-5
Molecular Formula: C23H26O3
Molecular Weight: 350.45
Appearance: Oil
Chemical Name: Potassium Castorate
CAS No.: 8013-05-6
Molecular Formula: C57H107K3O12
Molecular Weight: 1101.74718
Appearance: Yellow Liquid
Chemical Name: Di-n-amyl disulfide
Cas No.: 112-51-6
Molecular Fomula: C10H22S2
Molecular Weight: 206.41
评论
目前还没有评论。