benzyl (S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate RC00106

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:  www.cnroyalchem.com

【  Providing a complete set of intermediates and impurities for Lifitegrast  】

【  Providing a complete set of intermediates and impurities for Lifitegrast  】

【  Providing a complete set of intermediates and impurities for Lifitegrast  】

Product Details: Benzyl (S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

CAS Number:  1057218-08-2
Molecular Formula:  C₂₁H₂₄BrNO₄
Molecular Weight:  434.33 g/mol
Appearance:  White to off-white solid
Purity:  ≥95% (HPLC)
Storage Conditions:  Store at 2-8°C in a sealed container. Protect from light and moisture.

Chemical Structure & Key Features

Core Structure:

(S)-Configuration:  Chiral amino acid derivative.

Backbone:  3-(3-Bromophenyl)propanoic acid with benzyl ester protection.

Protecting Groups:

N-terminal:   tert -Butoxycarbonyl (Boc) group.

C-terminal:  Benzyl ester.

Bromine Substituent:  Meta-bromine on the phenyl ring enables cross-coupling reactions (e.g., Suzuki, Heck).

Applications

Peptide Synthesis:  Building block for Boc-protected peptides.

Medicinal Chemistry:  Intermediate for APIs (e.g., enzyme inhibitors, receptor modulators).

Chemical Biology:  Probe or linker in bioconjugation.

Handling & Safety

Safety Data Sheet (SDS):  Available upon request from suppliers.

Hazard Statements:

H315/H319: Causes skin/eye irritation.

H335: May cause respiratory irritation.

Precautionary Measures:  Use PPE (gloves, goggles) in a well-ventilated fume hood. 

Synthetic Route

Typically synthesized via:

Chiral Amino Acid Preparation:

Asymmetric hydrogenation of enolates or enzymatic resolution.

Protection Steps:

Boc-protection of the amine group.

Esterification with benzyl alcohol (DCC/DMAP catalysis).

Analytical Data

HPLC:  Retention time varies by method (C18 column, MeCN/H₂O gradient).

NMR (¹H, typical):

δ 7.40-7.10 (m, 8H, Ar-H), 5.15 (s, 2H, CH₂Ph), 4.40 (m, 1H, α-CH), 3.10 (dd, 2H, β-CH₂), 1.40 (s, 9H, Boc).

MS (ESI+):   m/z  435.1 [M+H]⁺. 

Regulatory Information

REACH:  Compliant for research use.

Customs:  Export may require controlled substance screening (bromine content).

Notes for Users

Purification:  Recrystallize from EtOAc/hexane or use flash chromatography (SiO₂, 20-30% EtOAc/hexane).

Deprotection:  Boc group removable with TFA; benzyl ester cleaved by H₂/Pd-C.