118994-90-4 | Oxazole-5-carboxylic acid

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$8.00	$5.00
1g	97%	in stock	$8.00	$6.00
10g	97%	in stock	$45.00	$32.00
15g	97%	in stock	$67.00	$47.00
25g	97%	in stock	$95.00	$66.00

Description

• Catalog Number: AB50543
• Chemical Name: Oxazole-5-carboxylic acid
• CAS Number: 118994-90-4
• Molecular Formula: C4H3NO3
• Molecular Weight: 113.0715
• MDL Number: MFCD04114931
• SMILES: OC(=O)c1cnco1

Computed Properties

• Complexity: 104
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 8
• Hydrogen Bond Acceptor Count: 4
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 0.2

Upstream Synthesis Route

The upstream synthesis of Oxazole-5-carboxylic acid can be achieved through a few possible routes, but a common approach is via the cyclization of amino acid precursors. One such method involves the following steps:

1. **Serine Route**: Start with L-serine as a starting material. Protect the amino group with a protecting group such as Boc (tert-butoxycarbonyl) to obtain Boc-serine.

2. **Activation of Carboxylic Acid**: Convert the carboxylic acid group of Boc-serine into a more reactive intermediate, typically by forming an acid chloride using thionyl chloride (SOCl2).

3. **Cyclization**: Induce cyclization through nucleophilic attack by the amine on the acyl chloride to form the oxazole ring. This step often requires a base such as triethylamine (TEA) and may proceed via an intramolecular dehydration.

4. **Dehydration**: If the previous step does not induce sufficient dehydration, an additional dehydration step may be necessary, possibly using a dehydrating reagent like phosphorus oxychloride (POCl3).

5. **Deprotection**: Remove the Boc protecting group using an acid such as trifluoroacetic acid (TFA) to yield the free amino group.

6. **Oxidation**: Lastly, oxidize the free amino group to introduce the carboxylic acid functionality at the 5-position of the oxazole ring. This can be achieved by using an oxidation agent such as potassium permanganate (KMnO4) or Jones reagent (CrO3 in aqueous sulfuric acid).

The resulting product is Oxazole-5-carboxylic acid. The actual route and conditions may vary depending on the desired yield, purity, and scalability of the synthesis. It is also worth noting that alternative starting materials such as other amino acids or preformed oxazole rings may be used depending on the specific synthetic requirements.

Literature

• beta(2) and beta(3)-adrenoceptor inhibition of alpha(1)-adrenoceptor-stimulated Ca(2+) elevation in human cultured prostatic stromal cells.

  European journal of pharmacology 20070910