1994
DOI: 10.1016/s0040-4039(00)76895-x
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Efficient coupling of α,α-dimethyl amino acid using a new chloro imidazolidium reagent, CIP

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Cited by 67 publications
(24 citation statements)
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“…Most recently, we realized that this sterically hindered secondary amino coupling reaction can be easily improved using CIP/HOAT/ DIEA (CIP: 2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate; HOAT: 1-hydroxy-7-azabenzotriazol; DIEA: N,N-diisopropylethylamine) coupling conditions on solid-phase support. 34 The peptide was finally cleaved from the resin using a TFA/H 2 O/TIPS (90/5/5) (TIPS: triisopropylsilane) cocktail solution at room temperature in one hour. The deprotection of the t-butyl group on the Tyr side chain also was completed at this stage.…”
Section: Synthesis [65]-and [75]-bicyclo [23] -Leu-enkephalin Analmentioning
confidence: 99%
“…Most recently, we realized that this sterically hindered secondary amino coupling reaction can be easily improved using CIP/HOAT/ DIEA (CIP: 2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate; HOAT: 1-hydroxy-7-azabenzotriazol; DIEA: N,N-diisopropylethylamine) coupling conditions on solid-phase support. 34 The peptide was finally cleaved from the resin using a TFA/H 2 O/TIPS (90/5/5) (TIPS: triisopropylsilane) cocktail solution at room temperature in one hour. The deprotection of the t-butyl group on the Tyr side chain also was completed at this stage.…”
Section: Synthesis [65]-and [75]-bicyclo [23] -Leu-enkephalin Analmentioning
confidence: 99%
“…Then, catalytic hydrogenation, followed by the condensation of 5a-c with the corresponding isocyanates gave the desired urea derivatives 2c-s. Compound 2e was obtained by the condensation of 3 with 7 by using 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP) 9,10) as a condensation reagent.…”
Section: Chemistrymentioning
confidence: 99%
“…65 The reaction of 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP) (32) was employed with α-aminoisobutyric acid (Aib) (Scheme 14). 66 The efficiency of the reaction with 32 was highly enhanced by adding HOAt as an additive. (34) have been reported as coupling reagents for the preparation of fully protected dipeptides 67 and Nprotected amino alcohols (Scheme 15).…”
mentioning
confidence: 99%