Pyridine → HCID 131723951, compound

Temperature

-78 °C

The 3″-amide of L-Cys(Oallyl) was prepared following the general description of Example 5. To this 3″-amide (50 mg) and pyridine (44 μL) in CH2Cl2 (0.25 mL) at −50° C. was added neat (CF3SO2)2O(13 μL) dropwise down the side of the flask to pre-cool it. After the addition was complete, the solution was stirred at −78° C. for 10 min, then allowed to warm to 0° C. in an ice bath. The solution was aged for 7.5 h at 0° C. and L-cysteine ally ester (26 mg) in CH2Cl2 (0.1 mL) was added. The solution was allowed to warm to room temperature and was aged overnight. The solution was poured into saturated NaHCO3(aq), extracted with CH2Cl2 and dried (Na2SO4). The solution was filtered, concentrated under reduced pressure and pure 7,24-bis-O-triethylsilyl protected title compound was obtained following PTLC on silica gel (1×1000 μm plate) using 3/7 acetone/hexanes as eluant. The pure product thus obtained was characterized by 1H NMR.

1. temperatureto pre-cool it
2. additionAfter the addition
3. temperatureto warm to 0° C. in an ice bath
4. waitThe solution was aged for 7.5 h at 0° C.
5. temperatureto warm to room temperature
6. waitwas aged overnight
7. extractionextracted with CH2Cl2
8. dry with materialdried (Na2SO4)
9. filtrationThe solution was filtered
10. concentrationconcentrated under reduced pressure and pure 7,24-bis-O-triethylsilyl
11. customwas obtained
12. customThe pure product thus obtained

ORD record

ord-8b365156723b44128e53352899e23736

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06586452B1