Benzyl glycidyl ether

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Benzyl glycidyl ether



Chiral HPLC
Column: Chiralcel OD-H (0.46 x 25 cm)
Detection: UV (254 nm) (In a few cases 214 nm was used.)
Benzyl Glycidyl Ether Analysis
Eluent: 10% iPrOH:90% Hexanes
Flow rate: 1.0 mL/min
Retention times of the two enantiomers: 8.2 and 9.0 minutes
Typical percentages of the two enantiomers using catalyst synthesized using L-Tartaric acid: 98.7% (8.2 min RT), 1.3% (9.0 min RT)
Typical percentages of the two enantiomers using catalyst synthesized using D-Tartaric acid: 3.5% (8.2 min RT), 96.5% (9.0 min RT)
3-Benzyloxy-1,2-propanediol Analysis
Eluent: 15% iPrOH:85% Hexanes
Flow rate: 0.9 mL/min
Retention times of the two enantiomers: 11.1 and 13.1 minutes
Typical percentages of the two enantiomers using catalyst synthesized using L-Tartaric acid: 84.0% (11.1 min RT), 16.0% (13.1 min RT)
Typical percentages of the two enantiomers using catalyst synthesized using D-Tartaric acid: 2.7% (11.1 min RT), 97.3% (13.1 min RT)
Optical Rotation
Jacobsen reports that the R enantiomer of benzyl glycidyl ether is the major one remaining using the (R,R) catalyst. (This is the catalyst produced using the L-Tartaric acid.) For a sample with >99% ee he reports: []²⁶_D +10° (c 5.2, MeOH).
Jacobsen reports that the R enantiomer of the diol is the major one produced using the (R,R) catalyst. (This is the catalyst produced using the L-Tartaric acid.) For a sample with 95% ee he reports: []²³_D -1.4° (c 3.31, EtOH).





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ANAGLIPTIN

N-[2-[[2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino]-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide
CAS No.:	739366-20-2
Synonyms:	Anagliptin;
Formula:	C19H25N7O2
Exact Mass:	383.20700

Anagliptin chemically known as N-[2-[2-[2(S)-cyanopyrrolidin-l-yl]-2-oxoethylamino]- 2-methylpropyl]-2-methylpyrazolo[l,5-a]pyrimidine-6-carboxamide is represented by the structural formula:

Anagliptin is a dipeptidyl peptidase IV- inhibitor. United States Patent No 7345 1 80- (IJS' 180) discloses anagliptin.     Example 5: Synthesis of N-[2-2[2(S)-Cyano pyrrolidin-l-yl]-2-oxoethyIamino]-2- methyIpropyl]-2-methyaIpyrazoIo [1, 5-a] pyrimidine-6-carboxamide (I, anagliptin). 1H NMR (300 MHz, CDC1₃): δ 1.16 (s, 6H), 2.23(m, 4H), 2.54(s, 3H), 3.25-3.51 (m, 6H), 4.78 (m, 1H), 6.53 (s, 1H), 8.05 (s, 1H), 8.93 (s, 1H), 9.22(s, 1H) HPLC Purity: 99.71%, Chiral purity: 100%

.........WO2014147640A2




 Kato, M.; Oka, M.; Murase, T.; Yoshida, M.; Sakairi, M.; Yamashita, S.; Yasuda, Y.; Yoshikawa, A.; Hayashi, Y.; Makino, M.; Takeda, M.; Mirensha, Y.; Kakigami, T. Discovery and pharmacological characterization of N-[2-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)-2-methylpropyl]- 2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide hydrochloride (anagliptin hydrochloride salt) as a potent and selective DPP-IV inhibitor. Bioorg. Med. Chem. 2011, 19, 7221–7227. http://www.sciencedirect.com/science/article/pii/S0968089611007784


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