4-Nitrobenzyl (2S,4S)-2-(Dimethylcarbamoyl)-4-mercapto-1-pyrrolidinecarboxylate TCI N0828

Chemical Identity

CAS No.: 96034-64-9
PubChem: CID 10871907·SID 253661888
Formula: C15H19N3O5S
Molecular weight: 353.4 g/mol
Purity: >95.0%(HPLC)(T)
Reference databases: ECHA

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: (4-nitrophenyl)methyl (2S,4S)-2-(dimethylcarbamoyl)-4-sulfanylpyrrolidine-1-carboxylate
SMILES: CN(C)C(=O)[C@@H]1C[C@@H](CN1C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])S
InChIKey: VGLBNJWGUYQZHD-STQMWFEESA-N

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4-Nitrobenzyl (2S,4S)-2-(Dimethylcarbamoyl)-4-mercapto-1-pyrrolidinecarboxylate from TCI (catalogue number N0828) is a chiral pyrrolidine derivative. A 4-nitrobenzyloxycarbonyl (PNZ) group protects the ring nitrogen, and position 4 carries a free thiol group. The compound is known as a side-chain intermediate for carbapenem antibiotics, especially meropenem. In the laboratory it is a ready-to-use chiral building block. Chemists use it for coupling reactions through its mercapto group, and it also supports work in peptide chemistry and pharmaceutical chemistry.

Researchers choose this compound because its (2S,4S) stereochemistry is already fixed, so they do not have to build two chiral centres from scratch. The thiol group is a strong nucleophile and can attack electrophiles such as the enol phosphate derivatives found on the carbapenem core. The PNZ protecting group is stable under many reaction conditions and can generally be removed by catalytic hydrogenolysis at the final stage. The dimethylcarbamoyl group at position 2 gives the substitution pattern that the target structure needs, which makes the synthetic route shorter and more efficient.

In Indonesia, this compound is relevant to pharmaceutical chemistry research laboratories at universities and research institutions. It suits synthetic organic chemistry groups studying carbapenem-type antibiotic structures, postgraduate projects on chiral heterocyclic building blocks, and teams developing and optimising synthetic routes. Because its stereochemistry is already defined, research groups can concentrate on the coupling and deprotection steps instead of multi-step construction of the chiral pyrrolidine ring. This helps them use limited research time and resources more efficiently.

Related TCI products

Carbapenem side-chain synthesis: the compound is a known intermediate for the meropenem side chain, and its (2S,4S) configuration matches the stereochemistry the target structure requires.
Thiol-based coupling reactions: the free mercapto group at position 4 is strongly nucleophilic, so it can attack electrophiles such as enol phosphate derivatives on the carbapenem core.
Chiral building block studies: the stereochemistry at both centres is already fixed, so researchers can bring a defined chiral pyrrolidine unit into new molecules without asymmetric synthesis of their own.
Protecting group strategy research: the PNZ group on the ring nitrogen stays stable under many reaction conditions and can generally be removed by catalytic hydrogenolysis, which makes it useful for studying late-stage deprotection sequences.
Peptide and pharmaceutical chemistry research: this functionalised pyrrolidine carboxylate is a suitable scaffold for exploratory work on heterocyclic, amide-bearing structures in peptide chemistry and medicinal chemistry programmes.

Brand	TCI (catalogue number N0828)
CAS number	96034-64-9
Molecular formula	—
Purity	—
Category	Chemistry > Chemical Biology > Peptide Chemistry
Pack sizes	please check the product page or contact the sales team for available pack sizes
Physical form	not stated in the product data; see the TCI certificate of analysis or product label
Storage	follow the storage conditions on the TCI label and safety data sheet

Store this compound in its original, tightly closed container in a cool, dry, well-ventilated place, following the conditions on the TCI label and safety data sheet. Because it has a free thiol group, reduce exposure to air, moisture and oxidising agents, which can degrade the mercapto group over time. Reseal containers promptly after use. Handle the material inside a fume hood and wear suitable personal protective equipment, including a laboratory coat, safety glasses and chemical-resistant gloves. Avoid inhaling dust or vapours and avoid contact with skin and eyes. Read the safety data sheet before first use, and dispose of residues according to institutional chemical waste procedures.

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