182352-59-6 | tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$8.00	$5.00
250mg	95%	in stock	$15.00	$10.00
1g	95%	in stock	$38.00	$26.00
5g	95%	in stock	$97.00	$68.00
10g	95%	in stock	$193.00	$135.00
25g	95%	in stock	$480.00	$336.00
100g	95%	in stock	$1,878.00	$1,315.00

Description

• Catalog Number: AA97917
• Chemical Name: tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate
• CAS Number: 182352-59-6
• Molecular Formula: C9H13NO4
• Molecular Weight: 199.2038
• MDL Number: MFCD18914399
• SMILES: O=C(N1CC(=O)CC1=O)OC(C)(C)C

Computed Properties

• Complexity: 290
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• XLogP3: 0.6

Upstream Synthesis Route

The upstream synthesis of tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate can be represented in various synthetic routes. A common route involves the following steps:

1. Start with the reaction of diethyl malonate with a base like sodium ethoxide to generate the enolate anion of diethyl malonate.

2. This anion then undergoes alkylation with tert-butyl bromoacetate in the presence of a base like potassium carbonate (K2CO3), leading to the formation of tert-butyl α-bromo-diethylmalonate.

3. Perform hydrolysis of ester groups in the tert-butyl α-bromo-diethylmalonate by using a strong acid like hydrochloric acid (HCl), resulting in the corresponding dicarboxylic acid.

4. Decarboxylation of one of the acid groups occurs upon heating, which leads to the formation of tert-butyl α-bromoacetylcarboxylate.

5. Cyclization of tert-butyl α-bromoacetylcarboxylate is achieved via intramolecular nucleophilic substitution, usually facilitated by a base such as potassium carbonate (K2CO3), to form tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate.

6. Purification steps may follow, such as recrystallization or chromatography, to obtain the tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate in pure form.

This broad outline summarizes the key synthetic steps typically employed in a laboratory setting to produce tert-Butyl 2,4-dioxopyrrolidine-1-carboxylate. Each step may be subject to optimization depending on the specific conditions, reagents, and desired yields.