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

Kose, Aytekin; GUNDOGDU, Ozlem; Anıl, Derya; FISTIKCI, Meryem; Altundas, Ramazan; Seçen, Hasan; Kara, Yunus

doi:10.1002/hlca.201400181

Makale Tam Makale Uluslararası 2015

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

Aytekin Kose, Ozlem GUNDOGDU, Derya Anıl, Meryem FISTIKCI, Ramazan Altundas, Hasan Seçen, Yunus Kara

HELVETICA CHIMICA ACTA Cilt 98 · Sayı 2 · ss. 260–266 · 01.02.2015

DOI ile aç

Özet

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.

Atıf için künye

Kose, A., GUNDOGDU, O., Anıl, D., FISTIKCI, M., Altundas, R., Seçen, H., & Kara, Y. (2015). Enantiospecific Synthesis of (R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic Acid Using (S)-Serine as a Chiral Pool. HELVETICA CHIMICA ACTA, 98(2), 260–266. https://doi.org/10.1002/hlca.201400181

BibTeX

@article{kose2015-71410,
  author = {Kose, Aytekin and GUNDOGDU, Ozlem and Anıl, Derya and FISTIKCI, Meryem and Altundas, Ramazan and Seçen, Hasan and Kara, Yunus},
  title = {Enantiospecific Synthesis of (R)-3-Amino-4-(2,4,5-trifluorophenyl)butanoic Acid Using (S)-Serine as a Chiral Pool},
  journal = {HELVETICA CHIMICA ACTA},
  year = {2015},
  volume = {98},
  number = {2},
  pages = {260--266},
  issn = {0018-019X},
  doi = {10.1002/hlca.201400181},
  url = {https://akademik.atauni.edu.tr/yayinlar/71410-enantiospecific-synthesis-of-r-3-amino-4-245-trifluorophenylbutanoic-acid-using}
}