2-(tert-butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid RC00154

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:  2-(tert-Butoxycarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid
CAS Number:  851784-82-2

Synonyms

5,7-Dichloro-2-{[(tert-butoxy)carbonyl]amino}-3,4-dihydro-1H-isoquinoline-6-carboxylic acid

2-(Boc)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid

Boc-5,7-diCl-THIQ-6-COOH

tert-Butyl 5,7-dichloro-6-(carboxy)-3,4-dihydro-1H-isoquinoline-2(1H)-carboxylate (Systematic IUPAC name)
Molecular Formula:  C₁₅H₁₇Cl₂NO₄
Molecular Weight:  346.21 g/mol

Core Scaffold:  1,2,3,4-Tetrahydroisoquinoline (THIQ), a partially saturated bicyclic heteroaromatic system.

Substituents:

A  tert-butoxycarbonyl (Boc)  group attached to the nitrogen atom (N-2 position), serving as a protective group for the secondary amine.

Two chlorine atoms  at positions 5 and 7 on the aromatic ring.

A  carboxylic acid group  (-COOH) at position 6 on the aromatic ring.

Key Characteristics

Protecting Group:  The Boc group masks the amine functionality, enhancing stability and allowing selective reactions elsewhere on the molecule. It is readily removable under mild acidic conditions (e.g., TFA or HCl).

Functional Handles:

Carboxylic Acid (C-6):  Enables diverse derivatization, such as amide bond formation (peptide coupling), esterification, or salt formation.

Protected Amine (N-2):  Available for deprotection and subsequent modification after synthesis.

Chlorine Atoms (C-5 & C-7):  Provide sites for further functionalization via metal-catalyzed cross-coupling reactions (e.g., Suzuki, Stille, Buchwald-Hartwig) or nucleophilic aromatic substitution.

Chirality:  The tetrahydroisoquinoline scaffold contains a chiral center at C-1. The commercially available material is typically the  racemic mixture  [(±)-form] unless otherwise specified. Enantiopure forms may be synthesized or separated for specific applications.

Solubility:  Typically soluble in polar aprotic solvents (e.g., DMSO, DMF), chlorinated solvents (e.g., DCM), and alcohols. Limited solubility in water and non-polar solvents (e.g., hexane). Solubility can vary with purity and crystalline form.

Stability:  Stable under ambient conditions when stored properly.  Moisture-sensitive  due to the Boc group (can hydrolyze/decompose slowly). Light-sensitive. Store cold and dry.

Typical Applications

Medicinal Chemistry & Drug Discovery:  A crucial  building block  for synthesizing complex molecules targeting various therapeutic areas (e.g., CNS disorders, oncology, infectious diseases). The THIQ scaffold is pharmacologically privileged.

Pharmaceutical Intermediates:  Used in the multi-step synthesis of active pharmaceutical ingredients (APIs) or candidate drugs.

Chemical Biology:  Probe or ligand development for studying biological targets.

Organic Synthesis:  Versatile intermediate for constructing more elaborate heterocyclic systems or functionalized isoquinoline derivatives via manipulation of the carboxylic acid, chlorine atoms, or protected amine.

Storage & Handling

Storage Conditions:  Store at  2-8°C  (refrigerated) or  -20°C  (for long-term storage). Keep container tightly sealed in a cool, dry, well-ventilated place. Protect from moisture and light. Use desiccants.

Handling:  Handle with care using appropriate personal protective equipment (PPE) - lab coat, gloves, safety glasses. Use in a fume hood. Avoid inhalation of dust and contact with skin/eyes.