Synthesis of TFA-protected alpha-Amino Acid Chloride via a Vilsmeier Reagent for Friedel-Crafts Acylation

Tachrim, Zetryana Puteri; Oida, Kazuhiro; Ohashi, Fumina; Kurokawa, Natsumi; Wang, Lei; Suzuki, Takeyuki; Hashimoto, Makoto

doi:10.2174/1570178617666200207111127


Hokkaido University \| Library \| HUSCAP	Advanced Search		言語

	Home
	About HUSCAP
	Open Access Policy

	Browse by Author

Browse
	Communities & Collections

	Scholarly Journals
	Theses
	Doctoral Dissertations Listed by Graduate Schools
	Conference Procs.
	Events

	HUSCAP Senior (in Japanese)

	Societies

	Downloads (country)

For university staff
	How to post your papers to HUSCAP
	Publication of theses
	Helpline about theses publication

Open Archives Compliant

You can search our collection also at:
	Google
	Google Scholar
	CiNii
	IRDB
	OAIster
	NDLTD

Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Agriculture / Faculty of Agriculture >
Peer-reviewed Journal Articles, etc >

Synthesis of TFA-protected alpha-Amino Acid Chloride via a Vilsmeier Reagent for Friedel-Crafts Acylation

Files in This Item:

Lett.Org.Chem.17(8) p.645-653.pdf

281.65 kB

PDF

View/Open

Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/82842

Title:	Synthesis of TFA-protected alpha-Amino Acid Chloride via a Vilsmeier Reagent for Friedel-Crafts Acylation
Authors:	Tachrim, Zetryana Puteri Browse this author
	Oida, Kazuhiro Browse this author
	Ohashi, Fumina Browse this author
	Kurokawa, Natsumi Browse this author
	Wang, Lei Browse this author
	Suzuki, Takeyuki Browse this author →KAKEN DB
	Hashimoto, Makoto Browse this author →KAKEN DB
Keywords:	Vilsmeier reagent
	alpha-Amino acid chloride
	Friedel-Crafts acylation
	alpha-amino acid
	alpha-amino arylketone
	racemization
Issue Date:	Aug-2020
Publisher:	Bentham Science Publishers
Journal Title:	Letters in Organic Chemistry
Volume:	17
Issue:	8
Start Page:	645
End Page:	653
Publisher DOI:	10.2174/1570178617666200207111127
Abstract:	α-Amino acid chlorides are reactive coupling agents in amide (peptide) formation. The Vilsmeier reagent ((chloromethylene)dimethylammonium chloride) offers a convenient way to prepare α-amino acid chlorides for peptide synthesis. Its use with N-trifluoracetyl (TFA)-protected isoleucine and allo-isoleucine is described. The 1H-NMR of the α-proton signal offers a convenient way to monitor the chirality retention in the acid chloride forming reaction and subsequent Friedel-Crafts acylation of arenes which result in α-amino acid aryl-ketone with no loss of chirality.
Rights:	The published manuscript is available at EurekaSelect via http://www.eurekaselect.com/openurl/content.php?genre=article&doi=10.2174/1570178617666200207111127.
Type:	article (author version)
URI:	http://hdl.handle.net/2115/82842
Appears in Collections:	農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 橋本誠

OAI-PMH ( junii2 , jpcoar_1.0 )

- Hokkaido University