Boc-Ala-OH

Boc-Ala-OH is a cornerstone reagent in peptide synthesis, serving as the standard building block for introducing alanine amino-acid residues via Boc SPPS. The Boc protecting group in Boc-Ala-OH masks the α-amino group during chain assembly, preventing premature reactions and enabling the formation of complex peptide sequences without side reactions. Beyond peptide synthesis, Boc-Ala-OH finds application in the preparation of N-propargylalanine — a key precursor for generating N-(3-aryl)propylated alanine residues — and in the resolution of racemic mixtures of chiral binaphthol derivatives. As a versatile chiral synthon, Boc-Ala-OH is also employed in the one-pot synthesis of hybrid tripeptidomimetics containing both amide and imide functionalities.

 

Product Parameters

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Parameter	Specification
Product Name	Boc-Ala-OH
CAS Number	15761-38-3
Molecular Formula	C₈H₁₅NO₄
Molecular Weight	189.21 g/mol
Appearance	White to almost white powder to crystal
Melting Point	79–83 °C (lit.)
Storage Condition	Sealed in dry,2-8°C
Density	1.2321
Boiling Point	324.46℃

Application

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Boc-Ala-OH is an amino acid derivative widely used in the preparation and synthesis of peptide-based pharmaceutical molecules and bioactive compounds. It also serves as a synthetic intermediate for biological macromolecules such as proteins, and is extensively applied in the production of fine chemicals including those used in biochemistry, food processing, and cosmetics.

 

Synthetic Route

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Under room temperature stirring, add a 2 N sodium hydroxide solution to the suspension of S-alanine (1.0 equivalents) in a mixture of dioxane and water (1:1, 100 mL). Transfer the resulting reaction mixture to an ice bath, cool it to 0°C, and stir for 15 minutes. Then add 10 mL of a dioxane solution containing (Boc)₂O (1.1 equivalents), and continue stirring the mixture at 0°C for another 45 minutes. Remove the ice bath and allow the mixture to return to room temperature; monitor reaction completion using a TLC monitor. After reaction completion, concentrate the mixture under reduced pressure, acidify the aqueous phase with citric acid (pH 2–3), extract three times with ethyl acetate, combine all organic layers, and wash each combined layer three times with saline solution. Separate the organic layers, dry them over Na₂SO₄, filter to remove the desiccant, and concentrate the filtrate under reduced pressure to obtain N-tert-butylcarbonyl-L-alanine.

 

Storage Conditions

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Store Boc-Ala-OH in a tightly sealed container in a cool, dark place at room temperature (recommended <15°C). Keep the container dry and protected from light. The compound should be stored away from strong oxidizing agents and strong bases.

 

Shelf life: When stored under recommended conditions in a sealed container, Boc-Ala-OH maintains its purity and optical activity for extended periods. Specific shelf life data is available upon request.

 

Handling precautions: Use in a well-ventilated area. Avoid dust formation. Wear chemical-resistant gloves, safety goggles, and a lab coat. After handling, wash hands thoroughly. Refer to the Safety Data Sheet (SDS) for complete safety information.

 

Contact Us

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Need Boc-Ala-OH for your peptide synthesis campaign or pharmaceutical intermediate manufacturing? Cosperpharm delivers the quality, documentation, and supply reliability you require. Reach out today to discuss your specifications, request a quote, or schedule a technical consultation.