Single-Step, Rapid, and Mild Synthesis of β-Amino Acid N-Carboxy Anhydrides Using Micro-Flow Technology

被引：15

作者：

Sugisawa, Naoto ^{[1
,2
]}

Otake, Yuma ^{[1
,2
]}

Nakamura, Hiroyuki ^{[1
]}

Fuse, Shinichiro ^{[1
,3
]}

机构：

[1] Tokyo Inst Technol, Inst Innovat Res, Lab Chem & Life Sci, Midori Ku, 4259 Nagatsuta Cho, Yokohama, Kanagawa 2268503, Japan

[2] Tokyo Inst Technol, Sch Life Sci & Technol, Midori Ku, 4259 Nagatsuta Cho, Yokohama, Kanagawa 2268503, Japan

[3] Nagoya Univ, Grad Sch Pharmaceut Sci, Dept Basic Med Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2020年 / 15卷 / 01期

基金：

日本学术振兴会;

关键词：

acylation; anhydrides; flow chemistry; beta-amino acids; INITIATED POLYMERIZATION; NCA POLYMERIZATION; FLASH CHEMISTRY; BASE STRENGTHS; PEPTIDES; MECHANISM; LEUCINE; DESIGN;

D O I：

10.1002/asia.201901429

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

beta-Amino acid N-carboxy anhydrides (beta-NCAs) are rarely used in the synthesis of beta-peptides, which is due mainly to the poor availability of these potentially useful substrates. Herein, we describe the heretofore challenging synthesis of beta-NCAs via a single-step, rapid, and mild formation using pH flash switching and flash dilution, which are aspects of micro-flow technology. We synthesized 15 beta-NCAs in good to excellent yields that included acid-labile beta-NCAs that cannot be readily synthesized using the conventional Leuchs approach. Scaled-up synthesis using this process can be readily achieved via continuous operation.

引用

页码：79 / 84

页数：6

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