Solvent-Free Mechanochemical Deprotection of N-Boc Group

نویسندگان

  • Mateja Đud
  • Davor Margetić
چکیده

Boc protection group could be readily removed in a very mild mechanochemical conditions. In a short reaction time, ball milling of Boc-protected amines with p-toluenesulfonic acid in solvent-free conditions affords corresponding amine p-TsOH salts.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Amino-functionalized (meth)acryl polymers by use of a solvent-polarity sensitive protecting group (Br-t-BOC)

We describe the synthesis of bromo-tert-butyloxycarbonyl (Br-t-BOC)-amino-protected monomers 2-((1-bromo-2-methylpropan-2-yl)oxycarbonylamino)ethyl (meth)acrylate 3a,b. For this purpose, 2-isocyanatoethyl (meth)acrylate 1a,b was reacted with 1-bromo-2-methylpropan-2-ol (2a). The free radical polymerization of (Br-t-BOC)-aminoethyl (meth)acrylates 3a,b yielded poly((Br-t-BOC)-aminoethyl (meth)ac...

متن کامل

Efficient Synthesis and Deprotection of Semicarbazones under Solvent-Free Conditions

Effective methodologies for efficient preparation of semicarbazones from aldehydes or ketones via milling and the subsequent regeneration of the parent carbonyls by gaseous nitrogen dioxide are described under solid-solid and gas-solid reaction conditions, respectively. These methods are fast, simple and environmentally benign which do not require the use of any auxiliaries such as catalyst...

متن کامل

A mechanochemical approach to access the proline–proline diketopiperazine framework

Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline-proline dipeptides under solvent-free conditions. A deprotection-cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stere...

متن کامل

Efficient microwave assisted syntheses of 2,5-diketopiperazines in aqueous media.

Aqueous in situ one-pot N-Boc-deprotection-cyclization of N alpha-Boc-dipeptidyl-tert-butyl and methyl esters under microwave irradiation afforded 2,5-diketopiperazines (DKPs) in excellent yields. This protocol is rapid, safe, environmentally friendly, and highly efficient, and showed that the tert-butoxy moiety is also an excellent leaving group for these cyclizations.

متن کامل

An Expedient Total Synthesis of Triciribine.

In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) gro...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2017