1-Boc-3-aMino-3-azetidinecarboxylic acid

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Cat Number

INT1262412134

CAS Number

1262412-13-4

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Product Detail Description Customer Q&A

CAS Number

1262412-13-4

Storage

2-8℃

Synonyms

3-amino-1-[(2-methylpropan-2-yl)oxycarbonyl]azetidine-3-carboxylic acid;1-(tert-butoxycarbonyl)-3-aminoazetidine-3-carboxylic acid

Molecular Formula

C9H16N2O4

Molecular Weight

216.23

Appearance

White to off-white powder

Boiling Point

350.2℃

Relative Density

1.29

pKa

1.9

General Description

1-Boc-3-amino-3-azetidinecarboxylic acid is a functionalized azetidine (four-membered nitrogen heterocycle) bearing both a carboxylic acid and a Boc-protected amino group on the same carbon of the ring (C-3). The azetidine ring is a constrained four-membered cyclic amine that serves as a conformationally restricted proline and pipecolic acid analog. The C-3 disubstitution creates a quaternary stereocenter at C-3, which is increasingly valued in modern drug design for improving target selectivity.

Mechanism of Action

1-Boc-3-amino-3-azetidinecarboxylic acid functions as a constrained amino acid building block in peptidomimetic drug design. The azetidine ring reduces the conformational flexibility of the backbone compared to pyrrolidine or piperidine, which can improve target selectivity and metabolic stability. The C-3 quaternary center (bearing NH-Boc and COOH) blocks metabolic cleavage at this position. The N-Boc group is stable under most conditions and removed under acidic conditions.

Application

1-Boc-3-amino-3-azetidinecarboxylic acid is used as a key intermediate in the synthesis of constrained peptide therapeutics, including HCV NS3/4A protease inhibitors (where the azetidine replaces a proline in the P2 position), integrin antagonists, and opioid receptor modulators. The C-3 amino-azetidine motif provides enhanced binding affinity and selectivity for serine and cysteine proteases. It is also used in the synthesis of functionalized chiral ligands for asymmetric catalysis.

What is the recommended storage condition for 1-Boc-3-aMino-3-azetidinecarboxylic acid?

It should be stored at 2-8°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for 1-Boc-3-aMino-3-azetidinecarboxylic acid?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

What is the primary synthetic application of 1-Boc-3-aMino-3-azetidinecarboxylic acid?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

Is 1-Boc-3-aMino-3-azetidinecarboxylic acid compatible with common organic solvents used in pharmaceutical synthesis?

Solubility and compatibility information is available in the technical data sheet. For specific solvent compatibility questions, please contact our technical team.

Is 1-Boc-3-aMino-3-azetidinecarboxylic acid manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.