反应详情

L-phenylalanine t-butyl ester hydrochloride (Bachem Bioscience, Inc.) (1.0 g, 3.9 mmol) was suspended in ethyl acetate, washed with saturated NaHCO3 and brine, dried (MgSO4), filtered and the solvent removed in vacuo. This residue was dissolved in 20 mL of THF and 1.95 g (3.5 mmol) of 2'-(N-triphenylmethyl tetrazol-5-yl)-4-bromomethylbiphenyl (prepared as described in EP 0 324 377) and 0.54 mL (3.9 mmol) triethylamine were added. The reaction was stirred at room temperature for 5 days. The THF was removed in vacuo and the residue dissolved in ethyl acetate. This was extracted 3× with K2CO3 and 1× with brine, dried over (MgSO4), filtered, and the solvent removed in vacuo. The product was purified by silica gel chromatography eluting with ethyl acetate-hexanes to yield 0.61 g (25%) of a white glass.

1. washwashed with saturated NaHCO3 and brine
2. dry with materialdried (MgSO4)
3. filtrationfiltered
4. customthe solvent removed in vacuo
5. dissolutionThis residue was dissolved in 20 mL of THF
6. customThe THF was removed in vacuo
7. dissolutionthe residue dissolved in ethyl acetate
8. extractionThis was extracted 3× with K2CO3 and 1× with brine
9. dry with materialdried over (MgSO4)
10. filtrationfiltered
11. customthe solvent removed in vacuo
12. customThe product was purified by silica gel chromatography
13. washeluting with ethyl acetate-hexanes