Synthesis
DOI: 10.1055/a-2602-4547
paper

Industrializable Synthesis of Fmoc-Ala-Thr-OH Pseudodipeptide as a Key Intermediate of Peptide Drugs

Xi-An Li
a   Leshan Vocational and Technical College, Leshan 614000, P. R. of China
b   Mianyang Key Laboratory of Traditional Chinese Medicine Resources Developm-ent and Utilization, Sichuan College of Traditional Chinese Medicine, Mianyang 621010, P. R. of China
,
Li-rong Yue
a   Leshan Vocational and Technical College, Leshan 614000, P. R. of China
,
Jiao Xu
a   Leshan Vocational and Technical College, Leshan 614000, P. R. of China
,
Xiao-feng Liang
b   Mianyang Key Laboratory of Traditional Chinese Medicine Resources Developm-ent and Utilization, Sichuan College of Traditional Chinese Medicine, Mianyang 621010, P. R. of China
,
Meng-jiao Zhou
b   Mianyang Key Laboratory of Traditional Chinese Medicine Resources Developm-ent and Utilization, Sichuan College of Traditional Chinese Medicine, Mianyang 621010, P. R. of China
,
Dong-yan Hu
a   Leshan Vocational and Technical College, Leshan 614000, P. R. of China
,
Hua-zhong Ren
a   Leshan Vocational and Technical College, Leshan 614000, P. R. of China
,
Jia-fu Feng
a   Leshan Vocational and Technical College, Leshan 614000, P. R. of China
,
Guang-tian Han
a   Leshan Vocational and Technical College, Leshan 614000, P. R. of China
› Author Affiliations

We are grateful for financial support from the Education Department of Sichuan (GZJG2022-239), the Science and Technology Research Project of the Sichuan Provincial Administration of Traditional Chinese Medicine (2023MS334), Science and Technology Bureau of LeShan Town (24YYJC0016, 24YYJC0019), and Leshan Vocational and Technical College.


Abstract

A new process for industrially synthesizing Fmoc-Ala-Thr-OH pseudodipeptide, which is a key intermediate for the synthesis of peptide drugs, is presented in four steps in overall 46% yield from Fmoc-L-Ala-OH. The process did not use column chromatography, and the characteristic of dipeptide salting with some organic base was cleverly utilized for purification. The suitable organic base for forming salt with the dipeptide was found after screening, and finally the synthesis was completed by recrystallization. The whole synthesis process is beneficial to industrial production and cost control. The purity of the product was over 99%.

Supporting Information



Publication History

Received: 23 February 2025

Accepted after revision: 07 May 2025

Accepted Manuscript online:
07 May 2025

Article published online:
11 June 2025

© 2025. Thieme. All rights reserved

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany