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

Kose, Aytekin; GUNDOGDU, Ozlem; AKTAS, Derya; FISTIKCI, Meryem; Altundas, Ramazan; SEÇEN, Hasan; KARA, Yunus

doi:10.1002/hlca.201400181

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

Kose A., GUNDOGDU O., AKTAS D., FISTIKCI M., Altundas R., SEÇEN H., ...Daha Fazla

HELVETICA CHIMICA ACTA, cilt.98, sa.2, ss.260-266, 2015 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 98 Sayı: 2
Basım Tarihi: 2015
Doi Numarası: 10.1002/hlca.201400181
Dergi Adı: HELVETICA CHIMICA ACTA
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.260-266
Atatürk Üniversitesi Adresli: Evet

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.