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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 6
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Original Articles

A Simple Preparation of Chloromethyl Esters of the Blocked Amino Acids

Naoyuki Harada Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd., 2-2-50 Kawagishi, Toda, Saitama, 335, Japan
,
Mitsuya Hongu Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd., 2-2-50 Kawagishi, Toda, Saitama, 335, Japan
,
Takashi Tanaka Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd., 2-2-50 Kawagishi, Toda, Saitama, 335, Japan
,
Takayuki Kawaguchi Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd., 2-2-50 Kawagishi, Toda, Saitama, 335, Japan
,
Tomiki Hashiyama Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd., 2-2-50 Kawagishi, Toda, Saitama, 335, Japan
&
Kenji Tsujihara Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd., 2-2-50 Kawagishi, Toda, Saitama, 335, Japan
Pages 767-772 | Received 18 Aug 1993, Published online: 16 Feb 2007

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Luciano De Petrocellis & Aniello Schiano Moriello. (2013) 2-Amino-4-arylthiazole compounds as TRPA1 antagonists (WO 2012085662): a patent evaluation. Expert Opinion on Therapeutic Patents 23:1, pages 119-147.
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Paula Gomes, Maria Isabel Santos, Maria Joaquina Trigo, Raquel Castanheiro & Rui Moreira. (2003) Improved Synthesis of Amino Acid and Dipeptide Chloromethyl Esters Using Bromochloromethane. Synthetic Communications 33:10, pages 1683-1693.
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Bin Zheng, Masano Sugiyama, Martin D. Eastgate, Alan Fritz, Saravanababu Murugesan & David A. Conlon. (2012) Development of a Process for the Preparation of Chloromethyl Chlorosulfate. Organic Process Research & Development 16:11, pages 1827-1831.
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Xiaozhong Fu, Saihong Jiang, Chuan Li, Jian Xin, Yushe Yang & Ruyun Ji. (2007) Design and synthesis of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity. Bioorganic & Medicinal Chemistry Letters 17:2, pages 465-470.
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Joëlle Azéma, Brigitte Guidetti, Myriam Malet-Martino, Robert Martino & Christine Roques. (2006) Efficient approach to acyloxymethyl esters of nalidixic acid and in vitro evaluation as intra-ocular prodrugs. Bioorganic & Medicinal Chemistry 14:8, pages 2569-2580.
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Nicholas P. Power, Donald Bethell, Lee Proctor, Elliot Latham & Paul Dawson. (2004) Chloromethyl chlorosulfate: a new, catalytic method of preparation and reactions with some nucleophiles. Org. Biomol. Chem. 2:10, pages 1554-1562.
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Boguslaw Mudryk, Shanthi Rajaraman & Nachimuthu Soundararajan. (2002) A practical synthesis of chloromethyl esters from acid chlorides and trioxane or paraformaldehyde promoted by zirconium tetrachloride. Tetrahedron Letters 43:36, pages 6317-6318.
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H. Ouyang, R.T. Borchardt, T.J. Siahaan & D.G. Vander Velde. (2008) Synthesis and conformational analysis of a coumarinic acid‐based cyclic prodrug of an opioid peptide with modified sensitivity to esterase‐catalyzed bioconversion. The Journal of Peptide Research 59:4, pages 183-195.
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Hui Ouyang, Ronald T Borchardt & Teruna J Siahaan. (2002) Steric hindrance is a key factor in the coupling reaction of (acyloxy) alkyl-α-halides with phenols to make a new promoiety for prodrugs. Tetrahedron Letters 43:4, pages 577-579.
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R. Alan Jones. 2001. Quaternary Ammonium Salts. Quaternary Ammonium Salts 69 118 .
N. HARADA, M. HONGU, T. TANAKA, T. KAWAGUCHI, T. HASHIYAMA & K. TSUJIHARA. (2010) ChemInform Abstract: A Simple Preparation of Chloromethyl Esters (III) of the Blocked Amino Acids (I).. ChemInform 25:47.
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