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Succinimidyl carbonate reaction with amines

As alternatives to 4-nitrophenyl chloroformate, carbonyl diimidazole [100-102] or di-A-succinimidyl carbonate [103,104] can be used to convert polymeric alcohols into alkoxycarbonylating reagents suitable for the preparation of support-bound carbamates. Polystyrene-bound alkoxycarbonyl imidazole is less reactive than the corresponding 4-nitrophenyl carbonate, and sometimes requires heating to undergo reaction with amines. Additional activation of these imidazolides can be achieved by N-methylation (Entry 9, Table 14.7). [Pg.379]

Figure 378 A succinimidyl carbonate derivative of mPEG was first prepared through the use of phosgene to form a chloroformate intermediate. Reaction with NHS gives the amine-reactive succinimidyl carbonate— mPEG. Figure 378 A succinimidyl carbonate derivative of mPEG was first prepared through the use of phosgene to form a chloroformate intermediate. Reaction with NHS gives the amine-reactive succinimidyl carbonate— mPEG.
For the sake of increased stability and improved storage, somewhat less reactive alternatives have been prepared from the labile chloroformate. For example, 2-(trimethylsilyl)ethyl -succinimidyl carbonate has been used to prepare Teoc-protected amino acids in water or dioxane using sodium hydrogen carbonate or triethylamine as the base. - 2-(Trimethylsilyl)ethyl 4-nitrophenyl carbo-nate2 246 g commercially available reagent (mp 34-36 C) that reacts with amino acids in a mixture of aqueous sodium hydroxide and rert-butyl alcohol or dioxane. Simple amines can be acylated with triethylamine under anhydrous conditions [Scheme 8.105]. Teoc derivatives can also be prepared by an exchange reaction using an aryl carbamate derivative and 2-(trimethylsilyl)ethanol as shown in Scheme 8.106. ... [Pg.540]


See other pages where Succinimidyl carbonate reaction with amines is mentioned: [Pg.128]    [Pg.149]    [Pg.175]    [Pg.197]    [Pg.483]    [Pg.162]    [Pg.176]    [Pg.176]    [Pg.222]    [Pg.483]    [Pg.386]    [Pg.386]    [Pg.142]    [Pg.156]    [Pg.156]    [Pg.202]    [Pg.268]    [Pg.125]    [Pg.269]    [Pg.382]    [Pg.446]   
See also in sourсe #XX -- [ Pg.941 ]

See also in sourсe #XX -- [ Pg.611 ]

See also in sourсe #XX -- [ Pg.611 ]




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Amines carbon

Carbonate reactions with

Carbonates with amines

Reaction with amines

Reaction with carbon

Succinimidyl carbonates

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