Methyl (R)-2-acetamido-3-chloropropanoate

Name: Methyl (R)-2-acetamido-3-chloropropanoate
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CAS No. 18635-38-6
Cat. No. CS-0276629
Molecule weight179.60
Purity≥96%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Methyl (R)-2-acetamido-3-chloropropanoate|CS-0276629

Structure of 18635-38-6

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General Information

CAS No. 18635-38-6
Cat. No. CS-0276629
Purity ≥96%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₁₀ClNO₃
Molecular Weight 179.60
Synonym(s) N-Acethyl-3-chloro-L-serine Methyl ester
SMILES CC(N[C@H](C(OC)=O)CCl)=O

Description

Methyl (R)-2-acetamido-3-chloropropanoate is a chiral synthetic intermediate featuring a stereodefined α-amino acid backbone with orthogonal functional handles. The acetamido group provides a protected amine, while the chlorinated side chain enables downstream substitution or coupling reactions. This bench-stable derivative integrates readily into peptide-like architectures and supports efficient derivatization under mild conditions.

Application

Methyl (R)-2-acetamido-3-chloropropanoate serves as a stereochemically defined building block for the synthesis of β-amino acid derivatives and chiral heterocycles. Its acetamido and chloro groups enable selective functionalization, while the methyl ester facilitates downstream transformations. The compound exhibits good bench stability and is compatible with standard coupling and reduction protocols, making it valuable in medicinal chemistry workflows requiring controlled stereochemistry and functional group diversity.

Synthesis

Route1
- 17136-54-8
- 75-36-5
- ~%
- In-stock
  
  18635-38-6
References
- US4933361 A1, ;
Route2
- 2311-26-4
- ~%
- In-stock
  
  18635-38-6
References
- Arzneimittel-Forschung/Drug Research, , vol. 34, # 10 B p. 1399 - 1401

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 55.4
LogP -0.0971
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Amide

Building Blocks Functional Group Ester

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Fatty chain compounds

Key Words

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Methyl (R)-2-acetamido-3-chloropropanoate

CAS No. 18635-38-6

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