Chloroacetamido-C4-NHBoc

 CAS No.: 133264-58-1  Cat No.: BP-500740 4.5  

Chloroacetamido-C4-NHBoc is a bifunctional PROTAC linker building block featuring a chloroacetamide electrophile and a protected amine (Boc) separated by a four-carbon (C4) spacer. The chloroacetamide moiety is designed to undergo chemoselective nucleophilic substitution with thiol- or amine-containing handles on ligands or intermediate fragments, enabling stable covalent conjugation under standard PROTAC synthesis conditions. The C4 chain provides a defined linker length and conformational flexibility that can improve productive spatial alignment between the two binding modules of a PROTAC, supporting efficient formation of a ternary complex with the target protein and the E3 ligase. The Boc-protected amine serves as a controllable point for subsequent coupling steps after deprotection. This linker is valuable for constructing modular targeted protein degradation reagents where reproducible attachment chemistry and tunable geometry are critical for optimizing degradation potency and selectivity.

Chloroacetamido-C4-NHBoc

Structure of 133264-58-1

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PROTAC Linker
Molecular Formula
C₁₁H₂₁ClN₂O₃
Molecular Weight
264.75

* For research and manufacturing use only. Not for human or clinical use.

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IUPACName
tert-butyl N-[4-[(2-chloroacetyl)amino]butyl]carbamate
InChI Key
UQDJWNQBFWMQHQ-UHFFFAOYSA-N
InChI
InChI=1S/C11H21ClN2O3/c1-11(2,3)17-10(16)14-7-5-4-6-13-9(15)8-12/h4-8H2,1-3H3,(H,13,15)(H,14,16)
SMILES
CC(C)(C)OC(=O)NCCCCNC(=O)CCl

This chloroacetamide-based C4 linker is designed for efficient installation of amine-bearing warheads in targeted protein degradation (PROTAC) workflows. Its electrophilic chloroacetamide functionality enables reliable coupling to nucleophilic groups, supporting modular PROTAC synthesis and subsequent optimization of linker length and attachment geometry. The features and practical considerations for assembling PROTAC constructs using this linker are described in detail below.

Structure: The linker contains a chloroacetamide electrophile and a protected amine (Boc) that supports controlled reactivity. It features amide and carbamate functionalities, along with a flexible aliphatic C4 spacer that can tune conformational freedom and attachment distance in PROTAC architectures.

Reactivity: The chloroacetamide moiety is suitable for nucleophilic substitution by amines under standard organic synthesis conditions, forming a stable thioether-free amide-linked junction typical of PROTAC intermediate construction. Use compatible polar aprotic or mixed solvents, and maintain conditions that preserve the Boc protecting group until intentional deprotection. No special catalysts are generally required for the substitution step, but base selection should match the nucleophile strength and avoid side reactions.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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