Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1
N ‐9‐Fluorenylmethoxycarbonyl‐ (Fmoc) amino‐acid chlorides have been prepared by reaction of hydrogen chloride on purified mixed Fmoc‐amino acid‐monoalkyl carbonic acid anhydrides in dichloromethane. The products partially undergo subsequent conversion to the corresponding esters due to the presence...
Published in: | International Journal of Peptide and Protein Research |
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crwiley:10.1111/j.1399-3011.1991.tb01416.x 2024-06-02T08:05:10+00:00 Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 CHEN, FRANCIS M.F. LEE, YOUNG C. BENOITON, N. LEO 1991 http://dx.doi.org/10.1111/j.1399-3011.1991.tb01416.x https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1111%2Fj.1399-3011.1991.tb01416.x https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1399-3011.1991.tb01416.x en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor International Journal of Peptide and Protein Research volume 38, issue 2, page 97-102 ISSN 0367-8377 journal-article 1991 crwiley https://doi.org/10.1111/j.1399-3011.1991.tb01416.x 2024-05-03T10:54:46Z N ‐9‐Fluorenylmethoxycarbonyl‐ (Fmoc) amino‐acid chlorides have been prepared by reaction of hydrogen chloride on purified mixed Fmoc‐amino acid‐monoalkyl carbonic acid anhydrides in dichloromethane. The products partially undergo subsequent conversion to the corresponding esters due to the presence of the liberated alcohol, the extent depending on the nature of the alkyl group. Esterification occurred to 5–20% when the alkyl group was isopropyl. Anhydrides of monoisopropenyl carbonic acid which liberate acetone instead of an alcohol gave products uncontaminated with ester. The three components in a reaction mixture could be determined as the reaction progressed by normal phase high‐performance liquid chromatography of aliquots, which had been freed of excess hydrogen chloride, on a μ Porasil (underivatized silica) column using tert ‐butanol‐hexane (1.5:98.5) as solvent. Article in Journal/Newspaper Carbonic acid Wiley Online Library Freed ENVELOPE(164.333,164.333,-71.483,-71.483) International Journal of Peptide and Protein Research 38 2 97 102 |
institution |
Open Polar |
collection |
Wiley Online Library |
op_collection_id |
crwiley |
language |
English |
description |
N ‐9‐Fluorenylmethoxycarbonyl‐ (Fmoc) amino‐acid chlorides have been prepared by reaction of hydrogen chloride on purified mixed Fmoc‐amino acid‐monoalkyl carbonic acid anhydrides in dichloromethane. The products partially undergo subsequent conversion to the corresponding esters due to the presence of the liberated alcohol, the extent depending on the nature of the alkyl group. Esterification occurred to 5–20% when the alkyl group was isopropyl. Anhydrides of monoisopropenyl carbonic acid which liberate acetone instead of an alcohol gave products uncontaminated with ester. The three components in a reaction mixture could be determined as the reaction progressed by normal phase high‐performance liquid chromatography of aliquots, which had been freed of excess hydrogen chloride, on a μ Porasil (underivatized silica) column using tert ‐butanol‐hexane (1.5:98.5) as solvent. |
format |
Article in Journal/Newspaper |
author |
CHEN, FRANCIS M.F. LEE, YOUNG C. BENOITON, N. LEO |
spellingShingle |
CHEN, FRANCIS M.F. LEE, YOUNG C. BENOITON, N. LEO Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 |
author_facet |
CHEN, FRANCIS M.F. LEE, YOUNG C. BENOITON, N. LEO |
author_sort |
CHEN, FRANCIS M.F. |
title |
Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 |
title_short |
Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 |
title_full |
Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 |
title_fullStr |
Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 |
title_full_unstemmed |
Preparation of N‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 |
title_sort |
preparation of n‐9‐fluorenylmethoxycarbonylamino acid chlorides from mixed anhydrides by the action of hydrogen chloride 1 |
publisher |
Wiley |
publishDate |
1991 |
url |
http://dx.doi.org/10.1111/j.1399-3011.1991.tb01416.x https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1111%2Fj.1399-3011.1991.tb01416.x https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1399-3011.1991.tb01416.x |
long_lat |
ENVELOPE(164.333,164.333,-71.483,-71.483) |
geographic |
Freed |
geographic_facet |
Freed |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
International Journal of Peptide and Protein Research volume 38, issue 2, page 97-102 ISSN 0367-8377 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1111/j.1399-3011.1991.tb01416.x |
container_title |
International Journal of Peptide and Protein Research |
container_volume |
38 |
container_issue |
2 |
container_start_page |
97 |
op_container_end_page |
102 |
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1800749934179254272 |