Tert-butyl chlorosulfonylcarbamate

Base Information

• Chemical Name: Tert-butyl chlorosulfonylcarbamate
• CAS No.: 147000-89-3
• Molecular Formula: C5H10ClNO4S
• Molecular Weight: 215.658
• European Community (EC) Number: 899-761-7
• Nikkaji Number: J1.259.459C
• Mol file: 147000-89-3.mol

Synonyms:147000-89-3;tert-butyl chlorosulfonylcarbamate;tert-butyl N-chlorosulfonylcarbamate;Carbamic acid, N-(chlorosulfonyl)-, 1,1-dimethylethyl ester;N-Boc-sulfamoyl chloride;tert-butyl N-(chlorosulfonyl)carbamate;tert-Butyl (chlorosulfonyl)carbamate;MFCD15475085;tert-butyl(chlorosulfonyl)carbamate;tert-butyl[chlorosulfonyl]carbamate;tert-butyl [chlorosulfonyl]carbamate;n-(tert-butoxycarbonyl)sulfamoyl chloride;n-boc chlorosulfonamide;Cl-SO2-NH-Boc;N-Boc sulfamoyl chloride;SCHEMBL192415;t-butyl(chlorosulfonyl)carbamate;tert-butylchlorosulfonylcarbamate;tertbuyl[chlorosulfonyl]carbamate;tert butyl chlorosulfonylcarbamate;KAJZZLBZXOBEMD-UHFFFAOYSA-N;tert-butyl (chlorosulfonyl) carbamate;AKOS006333628;N-tert-butoxycarbonylsulfamoyl chloride;BS-52475;SY024657;CS-0147276;EN300-118173;F20722;[(1,1-dimethylethoxy)carbonyl]-sulfamoyl chloride;A929258;N-(Chlorosulfonyl)-carbamic acid 1,1-dimethylethyl ester;[(tert-Butoxycarbonyl)amino](chloro)dioxo-lambda6-sulfane;Chloro[[(1,1-dimethylethoxy)carbonyl]amino]-sulfane dioxide

Chemical Property of Tert-butyl chlorosulfonylcarbamate

Chemical Property:

• PKA: 0.65±0.40(Predicted)
• PSA: 84.34000
• Density: 1.383±0.06 g/cm3(Predicted)
• LogP: 2.27990
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 215.0019067
• Heavy Atom Count: 12
• Complexity: 260

Purity/Quality:

97% ^*data from raw suppliers

tert-butylN-chlorosulfonylcarbamate 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NS(=O)(=O)Cl
• General Description: CarbaMic acid, N-(chlorosulfonyl)-, 1,1-diMethylethyl ester (also known as N-Boc-sulfamoyl chloride) is a key intermediate in the synthesis of substituted N-hydroxysulfamides. It is prepared by reacting t-butanol with chlorosulfonylisocyanate (CSI) and serves as a versatile precursor for constructing protected N-hydroxysulfamides through reactions with O-TBDMS-protected hydroxylamines. CarbaMic acid, N-(chlorosulfonyl)-, 1,1-diMethylethyl ester facilitates further functionalization via alkylation under Mitsunobu or standard conditions, enabling the introduction of diverse alkyl groups. Its utility extends to the synthesis of complex targets such as bis- and cyclic N-hydroxysulfamides, highlighting its importance in medicinal and synthetic chemistry.

Technology Process of Tert-butyl chlorosulfonylcarbamate

There total 4 articles about Tert-butyl chlorosulfonylcarbamate 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: 100.0%

isocyanate de chlorosulfonyle (1189-71-5) + tert-butyl alcohol (75-65-0) → N-tert-butyloxycarbonylsulfamoyl chloride (147000-89-3)

Guidance literature:

In dichloromethane;

DOI:10.1007/s00726-009-0267-2

Reference yield:

isocyanate de chlorosulfonyle (1189-71-5) → N-tert-butyloxycarbonylsulfamoyl chloride (147000-89-3)

Guidance literature:

With tert-butyl alcohol; In dichloromethane; at 0 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2021.127781

Reference yield:

tert-butyl alcohol (75-65-0) → N-tert-butyloxycarbonylsulfamoyl chloride (147000-89-3)

Guidance literature:

In dichloromethane;

upstream raw materials:

isocyanate de chlorosulfonyle

tert-butyl alcohol

Downstream raw materials:

(S)-tert-butyl 2-((N-(tert-butoxycarbonyl)sulfamoyl)amino)-3-phenylpropanoate

<(S)(+)> methyl -phenylalaninate

C₂₃H₂₈N₂O₈S

methyl -glycinate

Refernces

Synthetic methodology for the preparation of N-hydroxysulfamides

10.1016/j.tetlet.2007.09.037

The research presents a convenient synthetic methodology for preparing a variety of substituted N-hydroxysulfamides, which are structurally similar to N-hydroxyureas, N-hydroxysulfonamides, and sulfamides and exhibit a wide range of biological activity. The key starting material, N-Boc-sulfamoyl chloride, was prepared by reacting t-butanol with chlorosulfonylisocyanate (CSI). This intermediate was then reacted with several O-TBDMS protected hydroxylamines in the presence of triethylamine to form protected N-hydroxysulfamides. These protected sulfamides were further alkylated using Mitsunobu conditions or standard alkylation conditions with alkyl halides to introduce different alkyl groups on the nitrogen atoms. The final deprotection to the desired N-hydroxysulfamides was achieved using trifluoroacetic acid (TFA) and hydrochloric acid (HCl) in methanol. The methodology was extended to synthesize more complex targets such as bis-N-hydroxysulfamides and cyclic N-hydroxysulfamides. Chemicals such as t-butanol, chlorosulfonylisocyanate, O-TBDMS protected hydroxylamines, triethylamine, PPh3, DEAD, alkyl alcohols, alkyl halides, and TFA played crucial roles in the synthesis process.