(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
Related Products
Chemical Name: o-Xylene
Synonyms: 1,2-Dimethylbenzene; ortho-xylene
CAS No.: 95-47-6
Molecular Formula: C8H10
Molecular Weight: 106.17
Chemical Name: Imazalil Sulfate
CAS No.: 58594-72-2
Molecular Formula: C14H14Cl2N2O.H2SO4
Molecular Weight: 395.26
Appearance: Solid
Chemical Name: UV-120
Other Name: (2’,4’-Di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate)
CAS No.: 4221-80-1
Molecular Fomula: C29H42O3
Molecular weight: 438.66
Assay: ≥99%（LC）
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: STODDARD SOLVENT
CAS No.: 64742-88-7
Appearance: Colorless or Light Yellow Liquid
Chemical Name: alpha-Hexylcinnamaldehyde
CAS No.: 101-86-0
Molecular Formula: C15H20O
Molecular Weight: 216.32
Appearance: Yellow Liquid
Product name:HYDROXYPROPYL GUAR HYDROXYPROPYLTRIMONIUM CHLORIDE
Purity:99%
Appearance:Light Yellow Powder
Package:Customized according to customer needs.
Sample:Available
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: D-PANTOTHENIC ACID
CAS No.: 79-83-4
Molecular Formula: C9H17NO5
Molecular Weight: 219.24
Appearance: Colorless or Light Yellow Oily Liquid
Chemical Name: 3-Chloroaniline
Synonyms: 1-Amino-3-chlorobenzene; m-Aminochlorobenzene; 3-Chlorobenzenamine; 3-Chlorophenylamine
CAS No.: 108-42-9
Molecular Formula: C6H6ClN
Molecular Weight: 127.57
Appearance: Colorless Liquid
Chemical Name: Diclazuril
CAS No.: 101831-37-2
Molecular Formula: C17H9Cl3N4O2
Molecular Weight: 407.64
Appearance: White Solid
Product name:Cyclopentane
Purity:96%
Appearance:White powder
Package:25kg/bag
Sample:Available
Reviews
There are no reviews yet.