862599-47-1 | Ethyl 2-chlorooxazole-5-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$28.00	$19.00
1g	95%	in stock	$32.00	$23.00
5g	95%	in stock	$152.00	$107.00
10g	95%	in stock	$300.00	$210.00

Description

• Catalog Number: AC11670
• Chemical Name: Ethyl 2-chlorooxazole-5-carboxylate
• CAS Number: 862599-47-1
• Molecular Formula: C6H6ClNO3
• Molecular Weight: 175.5697
• MDL Number: MFCD09475866
• SMILES: CCOC(=O)c1cnc(o1)Cl

Computed Properties

• Complexity: 153
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• XLogP3: 1.9

Upstream Synthesis Route

The upstream synthesis route of Ethyl 2-chlorooxazole-5-carboxylate involves several key steps starting with the appropriate building blocks. The synthesis can be initiated from 5-amino-2-chlorophenol as the starting material.

1. Protection of the amino group – The first step is the protection of the amino group present in 5-amino-2-chlorophenol to prevent any unwanted reactions. This can be done using a suitable protecting group such as a Boc (tert-Butyloxycarbonyl) group using di-tert-butyl dicarbonate in the presence of a base like triethylamine.

2. Carboxylation – The protected amino group allows for the regioselective carboxylation at the free ortho position relative to the chloro group. This can be accomplished through the Sandmeyer reaction, where the phenol is first diazotized using sodium nitrite and hydrochloric acid, then converted to the respective carboxylic acid via reaction with carbon dioxide under pressure.

3. Cyclization to form the Oxazole ring – The next step involves the cyclization of the carboxylic acid group with the protected amino group to form the oxazole ring. This can be done by heating the compound, typically in the presence of a dehydrating agent like POCl3, to induce the formation of the oxazole ring. The chloro substituent on the phenol is ortho to both amino and carboxy groups, which facilitates the cyclization.

4. Hydrolysis and deprotection – The Boc protecting group is then removed to unveil the primary amine. Hydrolysis can be carried out with strong acids, like HCl, which will also simultaneously hydrolyze the ethyl ester to the corresponding carboxylic acid.

5. Esterification – The conversion back to the ester, in this case, ethyl ester, is accomplished by treating the carboxylic acid with ethanol in the presence of a catalytic amount of an acid catalyst, like sulfuric acid or HCl, to obtain the Ethyl 2-chlorooxazole-5-carboxylate.

It should be noted that each step in this synthesis route requires appropriate reaction conditions, workup procedures, and analysis to ensure the desired product is obtained with adequate purity before proceeding to the next step. Careful consideration of the reactivity of functional groups and use of protective groups are crucial in the successful synthesis of Ethyl 2-chlorooxazole-5-carboxylate.