Description
N-Boc-L-proline is a synthetic intermediate. It has been used in the synthesis of enantioselective catalysts for aldol reactions and hepatitis C virus (HCV) NS5A inhibitors.
Chemical Properties
White to off-white microcrystalline powder
Uses
N-Boc-L-proline is used as an intermediate in organic synthesis. It is also used to prepare daclatasvir, which inhibits the hepatitis C virus (HCV) non-structural 5A (NS5A) protein. Further, it is used as a drug in the treatment of hepatitis C virus (HCV).
Preparation
Triethylamine (16.5 mL, 0.12 mmol) was added dropwise over a period of 10 min to a stirred, ice-cold suspension of l-proline (10.0 g, 8.7 mmol) in dichloromethane (200 mL) in a 500-mL three-necked, round-bottomed flask. A solution of Boc2O (28.3 g, 0.13 mmol) in dichloromethane (100 mL) was then added over a period of 10 min and the mixture was stirred for 2.5 h. Thereafter, 10% aqueous citric acid (50 mL) was added, and the dichloromethane layer was washed with saturated brine (2×50 mL) and with water (50 mL). After drying the organic phase over magnesium sulfate, the solvent was evaporated and the residue was taken up in hot ethyl acetate. Dilution of this solution with hexane gave the product, N-tertbutoxycarbonyl- L-proline (17.8 g, 95%); mp 138–140℃; TLC (silica gel): Rf=0:36 (EtOAc/MeOH, 1:1).
reaction suitability
reaction type: Boc solid-phase peptide synthesis
References
[1] ALBRECHT BERKESSEL Johann L Burkhard Koch. Proline-Derived N-Sulfonylcarboxamides: Readily Available, Highly Enantioselective and Versatile Catalysts for Direct Aldol Reactions[J]. Advanced Synthesis & Catalysis, 2004, 346 9-10: 1141-1146. DOI:
10.1002/adsc.200404126[2] JUNXING SHI . Synthesis and biological evaluation of new potent and selective HCV NS5A inhibitors[J]. Bioorganic & Medicinal Chemistry Letters, 2012, 22 10: Pages 3488-3491. DOI:
10.1016/j.bmcl.2012.03.089
