tert-butyl N-methyl-N-[(4-methylbenzenesulfonyl)oxy]carbamate

Base Information

• Chemical Name: tert-butyl N-methyl-N-[(4-methylbenzenesulfonyl)oxy]carbamate
• CAS No.: 25370-96-1
• Molecular Formula: C₁₃H₁₉NO₅S
• Molecular Weight: 301.364
• European Community (EC) Number: 843-541-5
• Mol file: 25370-96-1.mol

Synonyms:tert-butyl N-methyl-N-[(4-methylbenzenesulfonyl)oxy]carbamate;25370-96-1;[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino] 4-methylbenzenesulfonate;EN300-218054;tert-butylN-methyl-N-[(4-methylbenzenesulfonyl)oxy]carbamate

Chemical Property of tert-butyl N-methyl-N-[(4-methylbenzenesulfonyl)oxy]carbamate

Chemical Property:

• Melting Point: 69-72 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 377.1±35.0 °C(Predicted)
• Density: 1.219±0.06 g/cm3(Predicted)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 301.09839388
• Heavy Atom Count: 20
• Complexity: 427

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)ON(C)C(=O)OC(C)(C)C

Technology Process of tert-butyl N-methyl-N-[(4-methylbenzenesulfonyl)oxy]carbamate

There total 2 articles about tert-butyl N-methyl-N-[(4-methylbenzenesulfonyl)oxy]carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.8%

di-tert-butyl dicarbonate (24424-99-5) + N-methylhydroxyamine hydrochloride (4229-44-1) + p-toluenesulfonyl chloride (98-59-9) → O-(p-toluenesulfonyl)-N-tert-butoxycarbonyl-N-methylhydroxylamine (25370-96-1)

Guidance literature:

di-tert-butyl dicarbonate; N-methylhydroxyamine hydrochloride; With potassium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 5h; Inert atmosphere; Cooling with ice;

p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1039/d0ob02122a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → O-(p-toluenesulfonyl)-N-tert-butoxycarbonyl-N-methylhydroxylamine (25370-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / potassium carbonate / tetrahydrofuran; H₂O / 5 h / 0 - 20 °C

2: 76 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

With potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol701774y

Reference yield: 97.0%

O-(p-toluenesulfonyl)-N-tert-butoxycarbonyl-N-methylhydroxylamine (25370-96-1) → O-(p-toluenesulfonyl)-N-methylhydroxylamine (25370-97-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h;

upstream raw materials:

di-tert-butyl dicarbonate

N-methylhydroxyamine hydrochloride

p-toluenesulfonyl chloride

Downstream raw materials:

O-(p-toluenesulfonyl)-N-methylhydroxylamine

2-oxoheptyl 4-methylbenzenesulfonate

2-oxopropyl tosylate

2-(tosyloxy)cyclohexanone

Refernces

• 1、 Paudyal, Mahesh P.,Wang, Mingliang,Siitonen, Juha H.,Hu, Yimin,Yousufuddin, Muhammed,Shen, Hong C.,Falck, John R.,Kürti, László. "Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles". supporting information. p. 557 - 560. Retrieved 2021/02/06.
• 2、 Tamura, Yasumitsu,Ikeda, Hiroyuki,Morita, Iwao,Tsubouchi, Hidetsugu,Ikeda, Masazumi. "O-Arenesulfonyl-N-alkylhydroxylamines as Aminating Reagents". . p. 1221 - 1224. Retrieved 2007/10/02.