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Organic-fluorous phase switches: A fluorous amine scavenger for purification in solution phase parallel synthesis

Linclau, B and Sing, AK and Curran, DP (1999) Organic-fluorous phase switches: A fluorous amine scavenger for purification in solution phase parallel synthesis. Journal of Organic Chemistry, 64 (8). 2835 - 2842. ISSN 0022-3263

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Abstract

The synthesis of the fluorous amine scavenger [(C6F13CH2CH2)3SiCH2CH2CH2]2NH and its successful application in the automated solution phase parallel synthesis of a urea library are described. Ureas were made by robotic synthesis from organic amines and excess isocyanates. The amine scavenger reacts with excess isocyanate, and the fluorous tag serves to solubilize the resulting adduct in the fluorous phase so it can be removed by fluorous-organic extraction. Organic urea products are isolated in high yields and purities after liquid-liquid extraction. Preliminary biological evaluation shows that several of the ureas have ion channel modulation abilities. In contrast to polymer and ionic quenching methods, the fluorous quench works whether the product is soluble or insoluble in the reaction medium, and ionizable functional groups are tolerated in the products.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Linclau, B
Sing, AK
Curran, DPcurran@pitt.eduCURRAN
Date: 16 April 1999
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 64
Number: 8
Page Range: 2835 - 2842
DOI or Unique Handle: 10.1021/jo9823442
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
PubMed ID: 11674353
Date Deposited: 18 Jul 2014 20:58
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/22327

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