Ethyl N-(mesitylsulfonyl)oxyacetimidate

Name: Ethyl N-(mesitylsulfonyl)oxyacetimidate
Brand: ChemScene
Availability: InStock
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CAS No. 38202-27-6
Cat. No. CS-W008041
Molecule weightNone
Purity≥95%
MDL No.MFCD00009244

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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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Ethyl N-(mesitylsulfonyl)oxyacetimidate|CS-W008041

Structure of 38202-27-6

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General Information

CAS No. 38202-27-6
Cat. No. CS-W008041
Purity ≥95%
MDL No. MFCD00009244
Storage -20°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₁₉NO₄S
Molecular Weight None
Synonym(s) O-Mesitylsulfonylacetohydroxamic Acid Ethyl Ester
SMILES C/C(OCC)=N\OS(=O)(C1=C(C)C=C(C)C=C1C)=O

Description

Ethyl N-(mesitylsulfonyl)oxyacetimidate serves as a robust, bench-stable reagent for C–H functionalization and amidation reactions. The mesitylsulfonyl group enhances electrophilicity while maintaining stability under standard conditions. This imidate ester integrates cleanly into synthetic sequences, enabling efficient coupling with nucleophiles and facilitating the construction of complex amide architectures in medicinal chemistry workflows.

Application

Ethyl N-(mesitylsulfonyl)oxyacetimidate serves as a reliable reagent for the efficient synthesis of α-aminoketones via imine formation and subsequent hydrolysis. Its mesitylsulfonyl group provides excellent stability and ease of purification, while the ethyl ester functionality enables straightforward derivatization. The compound functions effectively in mild conditions, offering high chemoselectivity and compatibility with diverse functional groups, making it a practical choice for synthetic intermediates in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  773-64-8
- In-stock
  
  10576-12-2
- ~89%
- In-stock
  
  38202-27-6
References
- BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John, F.; BENDER, John, A.; BENO, Brett, R.; GRANT-YOUNG, Katharine; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle, E.; YEUNG, Kap-Sun; CHUPAK, Louis, S. Patent: WO2011/112186 A1, 2011 ; Location in patent: Page/Page column 202 ; WO 2011/112186 A1
Route2
- In-stock
  
  10576-12-2
- 1667-04-5
- ~94%
- In-stock
  
  38202-27-6
References
- BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John F.; BENDER, John A.; BENO, Brett R.; GRANT-YOUNG, Katharine A.; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle E.; YEUNG, Kap-Sun; CHUPAK, Louis S. Patent: WO2010/30538 A2, 2010 ; Location in patent: Page/Page column 203 ;

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

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Computational Chemistry Data

TPSA 64.96
LogP 2.68706
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 4

Other Classifications

General Reagents Amination Reactions

Chemical Synthesis Synthetic Reagents C-X(Non-Halogen) Bond Formation Amination

Key Words

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Ethyl N-(mesitylsulfonyl)oxyacetimidate

CAS No. 38202-27-6

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