148017-28-1

Basic information

• Product Name: N-(tert-Butoxycarbonyl)sulfamide
• Synonyms: Carbamic acid, (aminosulfonyl)-, 1,1-dimethylethyl ester (9CI);Carbamic acid, N-(aminosulfonyl)-, 1,1-dimethylethyl ester;Carbamic acid, (aminosulfonyl)-, 1,1-dimethylethyl ester;N-(Aminosulfonyl)carbamic acid 1,1-dimethylethyl ester;N-(tert-Butoxycarbonyl)sulfamide;tert-butyl sulfamoylcarbamate;Boc-NHSO2NH2;tert-butyl N-sulfonylcarbaMate
• CAS NO: 148017-28-1
• Molecular Formula: C₅H₁₂N₂O₄S
• Molecular Weight: 196.22
• EINECS: 1533716-785-6
• Product Categories: N-BOC;Doripenem Intermediate
• Mol File: 148017-28-1.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.324
• Refractive Index: 1.494
• Storage Temp.: 2-8°C
• PKA: 5.00±0.40(Predicted)
• CAS DataBase Reference: N-(tert-Butoxycarbonyl)sulfamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butoxycarbonyl)sulfamide(148017-28-1)
• EPA Substance Registry System: N-(tert-Butoxycarbonyl)sulfamide(148017-28-1)

Safety Data

• Hazardous Substances Data: 148017-28-1(Hazardous Substances Data)

Usage

General Description

N-(tert-Butoxycarbonyl)sulfamide, also known as Boc-sulfamide, is a chemical compound used as a protecting group for amines in organic synthesis. It has a molecular formula of C5H11NO3S and a molecular weight of 169.21 g/mol. Boc-sulfamide is a white to off-white crystalline solid with a melting point of around 85-90°C. It is commonly used in peptide synthesis to protect the amine functional group from unwanted reactions during the synthesis process. Boc-sulfamide can be added to the amine group, and then removed under acidic conditions to reveal the free amine. This chemical has a wide range of applications in the pharmaceutical and chemical industries. It is important to handle Boc-sulfamide with care and follow proper safety protocols when working with this compound.

InChI:InChI=1/C5H12N2O4S/c1-5(2,3)11-4(8)7-12(6,9)10/h1-3H3,(H,7,8)(H2,6,9,10)

Upstream product

• 331839-52-2 benzyl N-(tert-butyloxycarbonyl)sulfamoylhydroxamate 
• 4248-19-5 tert-butyl carbazate 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 147000-89-3 N-tert-butyloxycarbonylsulfamoyl chloride 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 1167988-72-8 tert-butyl (E)-cinnamyl(sulfamoyl)carbamate 
• 491878-06-9 (2S,4S)-4-acetylthio-2-[[N-aminosulfonyl-N-(tert-butyloxycarbonyl)amino]methyl]pyrrolidine-1-carboxylic acid p-nitrobenzyl ester 

Relevant articles and documents

Practical one-pot synthesis of N-(tert-butoxycarbonyl)sulfamide from chlorosulfonyl isocyanate via N-(terf-butoxycarbonyl)aminosulfonylpyridinium salt

An efficient and practical process for the one-pot synthesis of N-(tert-butoxycarbonyl)sulfamide (4), a raw material for the aminosulfamoyl-containing side chain 3 of a novel carbapenem antibiotic doripenem hydrate (S-4661: 1), is described. In the previous process, chlorosulfonyl isocyanate was converted to N-(terf-butoxycarbonyl)aminosulfonyl chloride (7), an extremely unstable intermediate against moisture, which afforded the target compound 4 using liquid ammonia at cryogenic temperatures in 90% isolated yield. The use of liquid ammonia required cryogenic reaction temperatures because of heat generated from the highly exothermic reaction and the low boiling point of ammonia. In the improved process, the deactivation of the sulfonyl chloride 7 with pyridine at 0°C afforded water-resistant N-(tert-butoxycarbonyl)aminosulfonylpyridinium salt (8) which was converted in situ to the target compound 4 in the presence of water at 0°C in 90-96% isolated yields. Aqueous ammonia can be used, and no cryogenic temperatures are necessary for this new one-pot process.

Synthesis of 1,3-Diamines Through Rhodium-Catalyzed C-H Insertion

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INHIBITORS OF E1 ACTIVATING ENZYMES

This invention relates to compounds that inhibit El activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.