Cbz-cis-4-fluoro-Pro-OH synthesis
- Product Name:Cbz-cis-4-fluoro-Pro-OH
- CAS Number:72204-21-8
- Molecular formula:C13H14FNO4
- Molecular Weight:267.25
72180-14-4
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Yield:72204-21-8 97.53%
Reaction Conditions:
with lithium hydroxide in tetrahydrofuran at 25; for 14 h;
Steps:
13.B Step B:
N-Cbz-cis-4-fluor-L-methylprolinate (14.00 g, 49.03 mmol) was dissolved in THF (70.00 mL), LiOH solution (1 mol/L, 69.13 mL) was addedat 25°C and the mixture was stirred for 14 h at the same temperature.
The mixture was adjusted pH to 3 with hydrochloric acid solution (1 mol/L), added with water (200 mL) and extracted with EtOAc (200 mL X 4).
The organic phase was dried over anhydrous Na2SO4, filtered and the filtrate was concentrated at 45 °C in vacuo to give N-Cbz-cis-4-fluor-L-proline (13.00 g, 97.53%).
1HNMR (CDCl3, 400 MHz): δ 13.33-12.02 (m, 1H), 7.49-7.12 (m, 5H), 5.43-5.19 (m, 1H), 5.17-5.00 (m, 2H), 4.56-4.31 (m, 1H), 3.85-3.50 (m, 2H), 2.49-2.20 (m, 2H).
References:
EP3450430,2019,A1 Location in patent:Paragraph 0168; 0170
64187-48-0
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