The characteristics of Alloc-Cl(Allyloxycarbonyl chloride)

(2-hydroxyethyl)glycine tert-butyl ester (21) (0.60 g, 3.43 mmol) was attenuated in THF (10 ml) and pyridine (0.61 ml, 7.55 mmol) was added. Afterwards active the band-aid for 10 min and cooling to 0°C, Alloc-Cl(Allyloxycarbonyl chloride); 0.8 ml, 7.55 mmol) was added in portions over 30 min, while befitting the temperature beneath 5°C. The band-aid was accustomed to balmy to 22°C and was larboard active for 8 h. Afterwards complete about-face (TLC: silica, EtOAc/petroleum ether 55:45, Rf educt 0, Rf artefact 0.9, Rf mono-Alloc average 0.7), the THF was evaporated, baptize (50 ml) was added, and the artefact was extracted with CHCl3 (3 × 50 ml). The accumulated chloroform extracts were done with saturated NaHCO3 solution, HCl band-aid (1%), saturated NaCl band-aid and water, followed by dehydration over Na2SO4. The bread-and-butter was evaporated and the balance chromatographed on silica, eluting with EtOAc/petroleum ether (1:3) as an elution mixture. It has been appear that the Fmoc accumulation can be alien into amino acids application Alloc-Cl(Allyloxycarbonyl chloride) as acylating abettor beneath Schotten-Baumann altitude in the attendance of NaHCO3 or Na2CO3. However, the accumulation of adequate dipeptide contaminants in top bulk represents a absolute botheration in peptide chemistry. This ancillary artefact is difficult to ascertain by TLC but appears acutely on C18 chromatography.9It was approved that a simple condensate is not effective, authoritative the abatement of the contaminant a annoying and big-ticket process. Most of the reported methods are based on modifications of the acylating abettor acclimated for introducing the urethane-type attention groups. However, the new methods developed were added big-ticket than the chloroformate method.To extend this adjustment to added N-protecting amino groups,Alloc amino acids were prepared. Alloc-Gly-OH and AllocVal-OH were acquired application the azide adjustment in one-pot. Thus, starting from Alloc-Cl(Allyloxycarbonyl chloride) afterwards 1 h of acknowledgment with NaN3, allyloxycarbonyl azide (Alloc-N3) was obtained. Then, the chargeless amino acid, attenuated in 1% aqueous Na2CO3-dioxane, was added and afflicted for 48 h. The Alloc-Gly-OH and Alloc-Val-OH were acquired with acceptable yields and top purities (entries 19 and 20, Table 2). These were characterized abundantly by reversed-phase HPLC, TLC, and added concrete methods.
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