(S)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid

Name: (S)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid
Brand: ChemScene
Availability: InStock
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CAS No. 917027-02-2
Cat. No. CS-0154539
Purity≥97%
MDL No.MFCD07371721

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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(S)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid|CS-0154539

Structure of 917027-02-2

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General Information

CAS No. 917027-02-2
Cat. No. CS-0154539
Purity ≥97%
MDL No. MFCD07371721
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₆ClNO₄
Molecular Weight None
Synonym(s) N-Boc-S-4-Chlorophenylglycine
SMILES CC(C)(OC(N[C@H](C(O)=O)C1=CC=C(Cl)C=C1)=O)C

Description

This chiral building block features a protected (Boc) amine and a para-chlorophenyl group, enabling direct incorporation into peptide synthesis. The sterically hindered backbone enhances stability during coupling steps, while the electron-withdrawing chlorine improves reactivity in subsequent transformations.

Application

(S)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid serves as a key chiral building block for the synthesis of β-amino acid derivatives and peptidomimetics. The Boc-protected amine enables orthogonal functional group manipulation, while the para-chlorophenyl moiety provides structural rigidity and handles well under standard coupling conditions. This compound facilitates efficient peptide elongation and is compatible with diverse reaction conditions in medicinal chemistry workflows.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  6212-33-5
- ~%
- In-stock
  
  917027-02-2
- In-stock
  
  53994-85-7
References
- AMGEN INC.; BARTBERGER, Michael D.; BECK, Hilary Plake; CHEN, Xiaoqi; CONNORS, Richard V.; DEIGNAN, Jeffrey; DUQUETTE, Jason A.; EKSTEROWICZ, John; FOX, Brian M.; FU, Jiasheng; GONZALEZ BUENROSTRO, Ana; GONZALEZ LOPEZ DE TURISO, Felix; GUSTIN, Darin J.; HEATH, Julie A.; JOHNSON, Michael G.; KAYSER, Frank; KOPECKY, David J.; LI, Yihong; LI, Zhihong; MA, Zhihua; MCINTOSH, Joel; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; REW, Yosup; ROVETO, Philip M.; SCHMITT, Michael J.; SUN, Daqing; WANG, Xiaodong; WANSKA, Malgorzata; WEATHERS, Christine; YAN, Xuelei Patent: WO2013/49250 A1, 2013 ; Location in patent: Page/Page column 88 ;
Route2
- 1021948-10-6
- ~92%
- In-stock
  
  917027-02-2
References
- Arosio, Dario; Caligiuri, Antonio; D'Arrigo, Paola; Pedrocchi-Fantoni, Giuseppe; Rossi, Cristina; Saraceno, Caterina; Servi, Stefano; Tessaro, Davide Advanced Synthesis and Catalysis, 2007 , vol. 349, # 8-9 p. 1345 - 1348

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-P305+P351+P338-P330-P362+P364-P403+P233-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 Boc

Building Blocks Functional Group Chloride

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-((tert-Butoxycarbonyl)amino)-2-(4-chlorophenyl)acetic acid

CAS No. 917027-02-2

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