Di-f-butyl dicarbonate

Enol carbonates Di-f-butyl dicarbonate, 94 Potassium hexamethyldisilazide, 257 Enol esters Enol acetates Acetic anhydride, 93 Bis(7i5-cyclooctadienyl)ruthenium(II), 35... 

Write an equation for the protection of a given amino acid using di-f-butyl dicarbonate and for its deprotection using acid. 

RN — RNHBoc.2 Vicinal azido alcohols are converted directly into v/c-N-r-butoxycarbonylamino alcohols by Pd/C-catalyzed hydrogenation in the presence of di-f-butyl dicarbonate in ethyl acetate at 25°. Yields are 71-93%. 

BOC-AMINO ACIDS 2-f-Butoxycar-bonyloxyimino-2-phenylacetonitrile. Di-f-butyl dicarbonate. 

AMINO GROUP Boron trifluoride ether-ate. 1-/-B utyloxy carbony ltriazole-1,2,4. Di-f-butyl dicarbonate. 4-Dimethylamino-1-f-butyloxycarbonyl pyridinium chloride. CARBONYL GROUP Ceric ammonium nitrate. 1,2-Dihydroxy-3-bromopropane. Sodium N-chloro-p-toluenesulfonamide. Thallium(III) nitrate. Trichloroethanol. Trimethylsilyl cyanide. Chloromethyl methyl sulfide. N,N -Diisopropylhydra-zine. Trichloroethanol. 

The potassium compound 19 is readily transformed into 20 (R = alkyl) by the action of alkyl halides. The prodncts are converted into salts of aUcylamines RNH2 by acidic hydrolysis . Uses of di-f-butyl imidodicarboxylate (21) have been reviewed . Treatment of formamide with di-f-butyl dicarbonate 22 gives the unstable formyl compound 23, which yields 21 by the action of 2-diethylaminoethylamine (equation 18) ... 

Mioskowski and co-workers reported the use of Burgess salt, DAST, ox-alyl chloride and phosphorus oxychloride for dehydration of nitroaUcanes 13 among which they found DAST to be the best reagent [87]. Recently, a microwave-assisted generation of nitrile oxide 5 under the catalytic influence of 4-(4,6-dimethoxy[l,3,5]triazin-2-yl)-4-methylmorpholinium chloride (DMTMM)/DMAP [88] has been described. However, di-f-butyl dicarbonate (Boc20)/DMAP, a method reported by Basel and Hassner, allows the dehydration of nitroalkanes 13 under much milder conditions (Scheme 4) [89]. In fact, this has become an efficient method because of the innocuous nature of the side products (f-BuOH and CO2), which simplifies the purification of the ultimately desired isoxazoHne product. 

Many protecting groups are known, but in solid-phase peptide synthesis, the most frequently used N-protecting group is the t-butoxycarbonyl (Boc) group. The amino The most frequently used acid is protected by reaction with di-f-butyl dicarbonate. 

Di-f-butyl dicarbonate (B0C2O) Ethylene Chloroethylene Dimethyl Diethyl Dibutyltin oxide... 

Di-f-butyl dicarbonate (15.92 g, 69.30 mmol, 1.2 equiv) was slowly added to a solution of l//-indole-3-carbaldehyde (5.03 g, 36.40 mmol, 1 equiv) [245] and DMAP (0.43 g, 3.46 mmol, 10 mol %) in CH2CI2 (69 mL) [246]. The reaction mixture was stirred for 2 h. Then, the reaction mixture was diluted with CH2CI2 and washed with a sat. NH4CI solution. The aqueous phase was extracted 2 times with CH2CI2. Finally the organic phases were washed with brine, dried over MgSOa and concentrated. 6.39 g of tert-butyl 3-formyl-l//-indole-l-car-boxylate was isolated (75 %), which was used in the next step without further purification. 

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