(S)-methyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride RC00155

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 Name:  (S)-Methyl 2-amino-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride
CAS Registry Number:  851785-21-2
Synonyms:    

(S)-Methyl 3-(3-(methylsulfonyl)phenyl)-2-aminopropanoate hydrochloride

L-3-(3-(Methylsulfonyl)phenyl)alanine methyl ester hydrochloride

(S)-2-Amino-3-(3-(methylsulfonyl)phenyl)propionic acid methyl ester hydrochloride

Key features:

(S)-Configuration:  Chiral center at the alpha-carbon, indicating the L-enantiomer or (S)-absolute stereochemistry.

Core Structure:  Substituted phenylalanine derivative (α-amino acid ester).

Substituent:  Methylsulfonyl (-SO₂CH₃) group at the meta (3-) position of the phenyl ring.

Ester:  Methyl ester (-COOCH₃) at the C-terminus. 

Salt Form:  Hydrochloride (HCl) salt of the primary amine group.

Molecular Formula:  C₁₁H₁₅NO₄S · HCl
Molecular Weight:  293.77 g/mol (free base: 257.30 g/mol)
Solubility:

Soluble in polar organic solvents (e.g., DMSO, DMF, methanol, ethanol).

Partially soluble or sparingly soluble in water (due to the hydrophobic phenyl group).

Insoluble in non-polar solvents (e.g., hexane, diethyl ether). 

Storage Conditions:

Store at  2-8°C  (refrigerated) or  -20°C  for long-term stability.

Keep the container tightly sealed in a cool, dry, well-ventilated place.

Protect from moisture, light, and air to prevent degradation (potential for ester hydrolysis or racemization over time).

Store under an inert atmosphere (e.g., argon, nitrogen) if specified.

Handling Precautions:

Hazard Statements (H):  May cause skin irritation (H315), eye irritation (H319), and respiratory irritation (H335). Handle in accordance with good industrial hygiene and safety practice. 

Precautionary Statements (P):  Wear protective gloves/protective clothing/eye protection/face protection (P280). Use only outdoors or in a well-ventilated area (P271). IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing (P305+P351+P338). IF ON SKIN: Wash with plenty of soap and water (P302+P352). IF INHALED: Remove person to fresh air and keep comfortable for breathing (P304+P340).

Refer to the Safety Data Sheet (SDS):  Always consult the specific SDS provided by the supplier for comprehensive safety, handling, disposal, and regulatory information before use.

Applications:

Pharmaceutical Intermediate:  Primarily used as a chiral building block in the research and development of novel therapeutic agents. The methylsulfonylphenyl group is a common pharmacophore found in drugs targeting neurological disorders (e.g., serotonin/norepinephrine reuptake inhibitors - SNRIs), inflammation, and oncology.

Medicinal Chemistry Research:  Valuable for structure-activity relationship (SAR) studies, exploring modifications to the phenylalanine core for biological activity optimization.

Chemical Synthesis:  Employed as a chiral synthon in multi-step organic synthesis, particularly for introducing a chiral amino acid fragment with a meta-substituted aryl group bearing a polar sulfone moiety.

Biochemical Research:  Potentially used as a substrate or inhibitor in enzyme studies due to its structural similarity to phenylalanine.

Key Characteristics:

High Enantiopurity:  Essential for biological activity studies where stereochemistry is critical.

Functional Groups:  Contains a primary amine (as HCl salt), ester, and sulfone, offering diverse reactivity for further derivatization (e.g., amidation, reduction, nucleophilic substitution, coupling reactions).

Stability:  The hydrochloride salt form enhances stability and crystallinity compared to the free base. However, the ester group remains susceptible to hydrolysis under acidic/basic conditions or prolonged exposure to moisture.