tert-butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid

tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid is a premium chiral building block extensively utilized in organic synthesis and pharmaceutical research. The compound features a tert-butoxycarbonyl (Boc) protecting group, which is a cornerstone protecting strategy in peptide synthesis, allowing for selective deprotection under mild acidic conditions. The 4,4-difluorocyclohexyl moiety, when incorporated into larger molecular frameworks, significantly enhances the metabolic stability and lipophilicity of the final drug candidates—a critical consideration in optimizing pharmacokinetic profiles. tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid serves as an important intermediate in the synthesis of various bioactive compounds, including protease inhibitors and other therapeutic agents targeting specific enzymes. Its structure allows it to act as a prodrug or a building block for more complex molecules that can target specific receptors or enzymes in the body. The stereospecific (S)-configuration ensures enantiopurity—a non-negotiable requirement in modern pharmaceutical development where stereochemistry directly governs biological activity and safety profiles.

 

Product Parameters

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Parameter	Specification
Product Name	tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid
CAS Number	394735-65-0
Molecular Formula	C₁₃H₂₁F₂NO₄
Molecular Weight	293.31 g/mol
Melting Point	127.16 °C (calculated)
Boiling Point	410.7 ± 25.0 °C
Density	1.21 ± 0.1 g/cm³ (calculated)
Storage Condition	Store at room temperature
pKa	3.94±0.10

 

Product Advantages

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Enantiopure Chiral Building Block

tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid features a stereospecific (S)-configuration, ensuring enantiopurity for pharmaceutical applications where stereochemistry directly governs biological activity. The chiral center at the α-carbon is preserved through the Boc protection strategy, providing a reliable entry point for the synthesis of enantiomerically pure drug candidates.

 

 Boc Protection for Strategic Synthetic Flexibility

The tert-butoxycarbonyl (Boc) group is one of the most widely used amine protecting groups in organic synthesis, offering selective deprotection under mild acidic conditions (TFA or HCl) without affecting other acid-labile functionalities. This orthogonal protection strategy enables complex multi-step synthetic sequences, making tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid an ideal building block for peptide synthesis and medicinal chemistry.

 

 4,4-Difluorocyclohexyl Moiety for Enhanced Drug Properties

The geminal difluoro substituents on the cyclohexyl ring significantly enhance metabolic stability by blocking oxidative metabolism at the cyclohexyl positions. The fluorine atoms also increase lipophilicity, improving membrane permeability and bioavailability—critical parameters in drug design. This dual benefit of metabolic stabilization and enhanced pharmacokinetic properties makes the difluorocyclohexyl motif a valuable pharmacophore element.

 

 Versatile Intermediate for Bioactive Molecules

tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid serves as an important intermediate in the synthesis of protease inhibitors and other therapeutic agents targeting specific enzymes. The structure allows it to act as a building block for complex molecules that can target specific receptors or enzymes in the body.

 

 Ideal for Peptide Coupling and Drug Discovery

The carboxylic acid functionality enables straightforward peptide coupling reactions using standard reagents (DCC, HATU, EDCI, etc.). The compound is routinely employed in peptide synthesis and drug discovery processes, contributing to the creation of molecules with enhanced stability and bioavailability.

 

FAQ

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Q1: What is the stereochemistry of this compound?

A: tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid has an (S)-configuration at the α-carbon center. The stereospecificity is critical for pharmaceutical applications where enantiopurity is required.

 

Q2: Is this compound hazardous?

A: tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid is classified with hazard statements H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H332 (Harmful if inhaled). Signal word: Warning. Use in a fume hood with appropriate PPE—lab coat, safety goggles, and chemical-resistant gloves. Refer to the Safety Data Sheet (SDS) for complete safety information.

 

Product Quality Assurance

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Cosperpharm has established a comprehensive quality assurance system for tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid that meets the rigorous expectations of pharmaceutical research and development:

 

Thorough analytical characterization. Each batch undergoes multi-technique analytical release testing: HPLC purity verification (≥95% standard grade; ≥97–98% high purity grade, with full chromatographic traceability), appearance verification (white to off-white solid), and where applicable, ¹H NMR and MS confirmation of molecular identity. Chiral HPLC verification ensures the (S)-configuration is maintained.

 

Full batch traceability with retention samples. From raw material procurement through synthesis, purification, and final packaging, every step is fully documented and traceable. Each batch receives a unique lot number with sufficient retention samples maintained in accordance with Cosperpharm quality procedures.

 

Stability monitoring program. Cosperpharm conducts ongoing stability studies under recommended storage conditions (2–8 °C, sealed, dry). Stability summaries are updated regularly, with full data packages available to support customer research and development programs.

 

Documentation ready for research and development. Every shipment includes a Certificate of Analysis (COA) with batch-specific purity and characterization data, a Material Safety Data Sheet (SDS), and customs documentation for international delivery. For customers developing fluorinated drug candidates or peptide therapeutics, Cosperpharm provides additional documentation packages, method validation reports, stability data, and custom quality agreements upon request.

 

Customer-initiated quality audits. Qualified customers are welcome to audit Cosperpharm's manufacturing, quality control, and documentation facilities. Please contact our regulatory team to schedule an audit.

 

Contact Us

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Whether you are developing the next generation of protease inhibitors, optimizing peptide-based therapeutics, or building focused compound libraries for your medicinal chemistry program, securing reliable supplies of tert-Butoxycarbonylamino-(4,4-difluoro-cyclohexyl)-acetic acid should be the least of your concerns. Cosperpharm makes it straightforward—reach out today and let's discuss how we can support your research with quality chiral building blocks.