L-N-CBZ-3-PYRAZOL-1-YL-ALANINE synthesis
- Product Name:L-N-CBZ-3-PYRAZOL-1-YL-ALANINE
- CAS Number:20945-53-3
- Molecular formula:C14H15N3O4
- Molecular Weight:289.29
288-13-1
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Yield:20945-53-3 44%
Reaction Conditions:
in acetonitrile at 50; for 24 h;
Steps:
129.1
A suspension of (S) -benzyl 2 -oxooxetan-3 -ylcarbamate (0.67 g, 3.03 mmol} , and pyrazole (0.22 g, 3.29 mmol) in CH3CN (12 ?iL) was heated at 500C for 24h. The mixture was cooled' to rt overnight and the solid filtered to afford (S) -2- (benzyloxycarbonylamino) -3- (lH-pyrazol-1- yl) propanoic acid (330.1 mg) . The filtrate was concentrated in vacuo and then triturated with a small amount of CH3CN (ca. 4 mL) to afford a second crop (43.5 mg) . Total yield 370.4 mg (44%) . m.p. 165.5 - 168°C. lit m.p. 168.5 - 169.5 [Vederas et al . J. Am. Chem, Soc. 1985, 107, 7105] . 1HNMR (400 MHz, CD3OD) 5 7.51 {d, .J = 2.0, IH), 7.48 (s, J = 1.5 Hz, IH), 7.24 - 7.34 (m,5H), 6.23 m, IH), 5.05 (d, 12.7 H, IH), 5.03 (d, J = 12.7 Hz, IH), 4.59 - 4.66 (m, 2H), 4.42 - 4.49 (m, IH) . LCMS: Anal. Calcd. for C14H15N3O4: 289; found: 290 (M+H) + .
References:
WO2010/120621,2010,A1 Location in patent:Page/Page column 159; 160
172749-95-0
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20945-53-3
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