(6R,7R)-Benzhydryl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride

Name: (6R,7R)-Benzhydryl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride
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CAS No. 79349-53-4
Cat. No. CS-0197434
Purity≥97%
MDL No.MFCD00191256

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(6R,7R)-Benzhydryl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride|CS-0197434

Structure of 79349-53-4

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General Information

CAS No. 79349-53-4
Cat. No. CS-0197434
Purity ≥97%
MDL No. MFCD00191256
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₀Cl₂N₂O₃S
Molecular Weight 451.37
Synonym(s) (6R,7R)-7-AMino-3-(chloroMethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid DiphenylMethyl Ester Hydrochloride
SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)OC(=O)C3=C(CCl)CS[C@@H]4[C@@H](C(=O)N34)N.Cl

Description

This bench-stable, moisture-tolerant β-lactam derivative features a sterically hindered benzhydryl-protected amine and a reactive chloromethyl group at C3, enabling selective conjugation in late-stage functionalization. The para-nitro group enhances electrophilicity at the C8 carbonyl, facilitating nucleophilic attack under mild conditions.

Application

(6R,7R)-Benzhydryl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride serves as a key bicyclic β-lactam building block for synthesizing penem and carbapenem analogs. The chloromethyl group enables site-specific functionalization, while the amine and ketone functionalities support orthogonal derivatization. Bench-stable and compatible with standard peptide coupling and nucleophilic substitution protocols, it facilitates efficient access to diverse β-lactam scaffolds in medicinal chemistry campaigns.

Safety Information

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GHS Pictogram :	GHS No : GHS06,GHS08
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H317-H334
Precautionary Statements : P261-P272-P280-P285-P302+P352-P363-P501

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Computational Chemistry Data

TPSA 72.63
LogP 3.4763
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Ester

Building Blocks Skeleton Aliphatic heterocycle compounds Other aliphatic heterocycles compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(6R,7R)-Benzhydryl 7-amino-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate hydrochloride

CAS No. 79349-53-4

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