N-(tert-Butoxycarbonyl)-D-2-(4-chlorophenyl)glycine

Name: N-(tert-Butoxycarbonyl)-D-2-(4-chlorophenyl)glycine
Brand: ChemScene
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CAS No. 53994-85-7
Cat. No. CS-0067904
Purity≥98%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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N-(tert-Butoxycarbonyl)-D-2-(4-chlorophenyl)glycine|CS-0067904

Structure of 53994-85-7

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General Information

CAS No. 53994-85-7
Cat. No. CS-0067904
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₆ClNO₄
Molecular Weight 285.72
Synonym(s) N-Boc-(4'-Chlorophenyl)glycine
SMILES CC(C)(C)OC(N[C@H](C1=CC=C(C=C1)Cl)C(O)=O)=O

Description

N-(tert-Butoxycarbonyl)-D-2-(4-chlorophenyl)glycine serves as a key chiral building block in peptide synthesis, featuring a sterically protected N-terminal group and a para-chlorophenyl side chain. This configuration enhances stability during coupling steps and facilitates selective derivatization in complex molecule assembly.

Application

N-(tert-Butoxycarbonyl)-D-2-(4-chlorophenyl)glycine serves as a key chiral building block in the synthesis of peptidomimetics and pharmaceutical intermediates. Its tert-butoxycarbonyl (Boc) group provides robust protection for the amine, enabling orthogonal handling in multi-step sequences. The D-configured glycine moiety with a 4-chlorophenyl substituent offers a sterically defined, electron-deficient aryl handle suitable for cross-coupling reactions and incorporation into bioactive scaffolds. Bench-stable and readily purified by standard chromatography, it facilitates efficient access to complex molecular architectures in medicinal chemistry campaigns.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  6212-33-5
- ~92%
- In-stock
  
  53994-85-7
References
- CHIESI FARMACEUTICI S.p.A. Patent: US2012/134934 A1, 2012 ; Location in patent: Page/Page column 28 ;
Route2
- 124-38-9
- 774225-25-1
- ~%
- In-stock
  
  53994-85-7
- In-stock
  
  120157-95-1
References
- Angewandte Chemie - International Edition, , vol. 50, # 6 p. 1393 - 1396
Route3
- 124-38-9
- 1291065-80-9
- ~%
- In-stock
  
  53994-85-7
- In-stock
  
  120157-95-1
References
- Journal of Organic Chemistry, , vol. 77, # 5 p. 2159 - 2168

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 75.63
LogP 2.9904
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Life Science Amino Acids and their Derivatives Glycine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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N-(tert-Butoxycarbonyl)-D-2-(4-chlorophenyl)glycine

CAS No. 53994-85-7

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