(3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid

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Cat Number

INT1428243246

CAS Number

1428243-24-6

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Product Detail Description Customer Q&A

CAS Number

1428243-24-6

EINECS

820-324-3

Synonyms

1,3-Pyrrolidinedicarboxylic acid, 4-ethyl-, 1-(phenylmethyl) ester, (3R,4S)-;(3R,4S)-4-ethyl-1,3-Pyrrolidinedicarboxylic acid 1-(phenylmethyl) ester

Molecular Formula

C15H19NO4

Molecular Weight

277.32

Smiles

N1(C(OCC2=CC=CC=C2)=O)C[C@@H](CC)[C@@H](C(O)=O)C1

Boiling Point

443.9℃

Relative Density

1.2

pKa

4.48

General Description

(3R,4S)-1-((Benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid is a stereochemically defined, N-Cbz-protected pyrrolidine bearing both a carboxylic acid at C-3 and an ethyl substituent at C-4 of the five-membered nitrogen heterocycle. The (3R,4S) stereochemistry defines two adjacent stereocenters in a defined relative and absolute configuration. The N-Cbz (benzyloxycarbonyl) protecting group is stable under a broad range of conditions and removed by hydrogenolysis.

Mechanism of Action

(3R,4S)-1-((Benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid functions as a stereochemically defined, protected amino acid building block in peptidomimetic synthesis. The carboxylic acid can be coupled to amines, alcohols, or activated for further transformation. The N-Cbz group can be removed by hydrogenolysis (Pd/C, H2) to reveal the secondary amine. The two stereocenters at C-3 and C-4 impose defined conformational constraints on the resulting peptide mimetics.

Application

(3R,4S)-1-((Benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid is used as a stereochemically pure intermediate in the synthesis of peptidomimetic pharmaceuticals, including HIV protease inhibitors, renin inhibitors, and alpha-glucosidase inhibitors. The constrained pyrrolidine carboxylate scaffold is found in several marketed drugs. It is also used in the synthesis of chiral catalysts and resolving agents.

What is the recommended storage condition for (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid?

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

Can we obtain batch-specific analytical data for (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid?

Batch-specific COA documents are standard with every shipment. Additional analytical reports, including HPLC chromatograms or spectral data, may be provided upon request.

Can (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid be provided with custom specifications for synthetic applications?

Custom specifications including adjusted particle size, solvent residue limits, or additional purity testing can be arranged for qualified customers with defined requirements.

What scale of supply is available for (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid for pilot or commercial synthesis?

Supply is available from laboratory research scale through multi-kilogram pilot quantities. Commercial-scale supply can be discussed based on projected demand.

What quantities of (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid are available for order?

We accommodate orders of varying scale, from small research quantities through bulk commercial supply. Contact our sales team to discuss pack sizes and volume pricing.