Enantiospecific Synthesis of (R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic Acid Using (S)-Serine as a Chiral Pool

被引：3

作者：

Kose, Aytekin ^{[1
]}

Gundogdu, Ozlem ^{[1
]}

Aktas, Derya ^{[1
]}

Fistikci, Meryem ^{[1
]}

Altundas, Ramazan ^{[1
]}

Secen, Hasan ^{[1
]}

Kara, Yunus ^{[1
]}

机构：

[1] Ataturk Univ, Dept Chem, Fac Sci, TR-25240 Erzurum, Turkey

来源：

HELVETICA CHIMICA ACTA | 2015年 / 98卷 / 02期

关键词：

ASYMMETRIC-SYNTHESIS; IV INHIBITOR; SITAGLIPTIN;

D O I：

10.1002/hlca.201400181

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Starting from (S)-serine, a new method was developed for the synthesis of the beta-amino acid part of sitagliptin in ten steps and with an overall yield of 30%. The crucial step of the synthesis was the ring opening of N-and O-protected (R)-aziridin-2-methanol with (2,4,5-trifluorophenyl) magnesium bromide to give N-and O-protected (R)-2-amino-3-(2,4,5-trifluorophenyl) propan-1-ol.

引用

页码：260 / 266

页数：7

共 50 条

[1] Efficient Synthesis of 3-R-Boc-amino-4-(2,4,5-trifluorophenyl)butyric Acid
Pan, Xianhua
Bai, Shupei
Yu, Wansheng
Ding, Ding
Zhao, Dongxian
Liu, Feng
SYNTHETIC COMMUNICATIONS, 2015, 45 (12) : 1451 - 1456
[2] Preparation of Menthyl 3-amino-4-(2,4,5-trifluorophenyl) Butyrate and Investigation of its Hypoglycemic Activity
Kuang, Xinmou
Su, Minru
Li, Hao
Sheng, Xiaolan
Cai, Huan
Xie, Shuilin
Liu, Zhonghua
CURRENT MOLECULAR MEDICINE, 2024, 24 (12) : 1550 - 1556
[3] Improved Synthesis of (R)-3-(t-Butoxycarbonylamino)-4-(2,4,5-trifluorophenyl) butanoic Acid as a Key Intermediate for the Synthesis of Sitagliptin
Kwak, Woo Young
Mok, Hui Yeon
Yoon, Sung-Hwa
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2017, 38 (08): : 976 - 979
[4] Novel and enantioselective syntheses of (R)- and (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanoic acid: a synthon for sitagliptin and its derivatives
Fistikci, Meryem
Gundogdu, Ozlem
Aktas, Derya
Secen, Hasan
Sahin, M. Fethi
Altundas, Ramazan
Kara, Yunus
TETRAHEDRON, 2012, 68 (12) : 2607 - 2610
[5] Synthesis of (R)-3-(tert-Butoxycarbonylamino)-4-(2,4,5-trifluorophenyl)butanoic Acid, a Key Intermediate, and the Formal Synthesis of Sitagliptin Phosphate
Sreenivasulu, Kurella
Chaudhari, Pramod S.
Achanta, Srinivas
Sud, Abhishek
Dahanukar, Vilas
Cobley, Christopher J.
Llewellyn-Beard, Fiona
Bandichhor, Rakeshwar
CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (10) : 1605 - 1608
[6] Thermodynamic Models for Determination of the Solubility of Boc-(R)-3-Amino-4-(2, 4, 5-trifluorophenyl)butanoic acid in Different Pure Solvents and (Tetrahydrofuran plus n-Butanol) Binary Mixtures with Temperatures from 280.15 to 330.15 K
Fan, Shimin
Yang, Wenge
Guo, Qirun
Hao, Jianfeng
Li, Hongjie
Yang, Shouhai
Hu, Yonghong
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2016, 61 (03): : 1109 - 1116
[7] (3R)-4-1(3R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(2,2,2-trifluoroethyl)-1,4-diazepan-2-one, a selective dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
Biftu, Tesfaye
Feng, Dennis
Qian, Xiaoxia
Liang, Gui-Bai
Kieczykowski, Gerard
Eiermann, George
Huaibing, He
Lelting, Barbara
Lyons, Kathy
Petrov, Aleksandr
Sinha-Roy, Ranabir
Zhang, Bei
Scapin, Giovanna
Patel, Sangita
Gao, Ying-Duo
Singh, Suresh
Wu, Joseph
Zhang, Xiaoping
Thornberry, Nancy A.
Weber, Ann E.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (01) : 49 - 52
[8] Design and Synthesis of 4-(2,4,5-Trifluorophenyl)butane-1,3-diamines as Dipeptidyl PeptidaseIV Inhibitors
Zhu, Linrong
Li, Yuanyuan
Qiu, Ling
Su, Mingbo
Wang, Xin
Xia, Chunmei
Qu, Yi
Li, Jingya
Li, Jia
Xiong, Bing
Shen, Jingkang
CHEMMEDCHEM, 2013, 8 (07) : 1104 - 1116
[9] (3R,4S)-4-(2,4,5-Trifluorophenyl)-pyrrolidin-3-ylamine inhibitors of dipeptidyl peptidase IV: Synthesis, in vitro, in vivo, and X-ray crystallographic characterization
Wright, Stephen W.
Ammirati, Mark J.
Andrews, Kim M.
Brodeur, Anne M.
Danley, Dennis E.
Doran, Shawn D.
Lillquist, Jay S.
Liu, Shenping
McClure, Lester D.
McPherson, R. Kirk
Olson, Thanh V.
Orena, Stephen J.
Parker, Janice C.
Rocke, Benjamin N.
Soeller, Walter C.
Soglia, Carolyn B.
Treadway, Judith L.
VanVolkenburg, Maria A.
Zhao, Zhengrong
Cox, Eric D.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (20) : 5638 - 5642
[10] Synthesis, antibacterial activity, and docking studies of some novel N'-benzylidene-2-(2,4,5-trifluorophenyl)acetohydrazides
Ramesh, Navudu
Rao, Mannem Gangadhara
Babu, A. Vasu
Nagababu, P.
Rao, V. Umamaheswara
Babu, B. Hari
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (07) : 4145 - 4164

← 1 2 3 4 5 →