Alcohols immobilization onto 2-chlorotritylchloride resin under microwave irradiation

Tetrahedron Letters

Volumn 52, Issue 22, 2011, Pages 2808-2811

  Rizzi, Luca ^a   Cendic, Katarina ^a   Vaiana, Nadia ^a   Romeo, Sergio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

2 Chlorotritylchloride resin; Alcohol; Cyclic peptide; Microwave; Solid phase synthesis

Indexed keywords

AMINOALCOHOL; BASE; CHLORIDE; CYCLOPEPTIDE; ETHANOLAMINE; HYDROXYL GROUP; RESIN; TYRAMINE;

ARTICLE; BINDING KINETICS; IMMOBILIZATION; MICROWAVE IRRADIATION; REACTION TIME; SOLID PHASE SYNTHESIS; TEMPERATURE;

EID: 79955550097     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.113     Document Type: Article

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25. 301 = 7800). UV measurements were carried out with a Unicam Heλios α spectrophotometer.
26. 2, was added to the reactor. Then the appropriate base (10 equiv) was added and the reaction was stirred in sealed reactor under MW irradiation. At the end of the reaction the excess of reagents was filtered off and the resin was washed with DMF (6 times). To cleave the Fmoc-group, a solution of piperidine (20% in DMF) was added to the resin and the mixture was swirled for 5 min at rt and filtered. Then, another amount of piperidine (20% in DMF) was added and the mixture swirled for other 15 min. The excess of reagents was initially filtered off and successively the resin was washed with DMF (6 times). MW reactions were carried out by Biotage Initiator oven.
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28. At the end of the MW reaction, methanol was added to the mixture, in order to cap the unreacted chloride groups, and the reaction mixture was stirred for 5 min. Then, the excess of reagents was filtered off and the resin was washed with DMF (6 times). A solution of FmocGlyOH (4 equiv), TBTU (4 equiv, 0.45 M in DMF) and DIPEA (10 equiv) was added to the resin and the mixture was stirred for 50 min. At the end of the reaction the excess of reagents was filtered off and the resin was washed with DMF (6 times) and piperidine (20% in DMF) was added to the resin to cleave the Fmoc group.
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