L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- → 2-Amino-3-benzoyl-6-[2-t-butoxycarbonylamino-3-(4-hydroxyphenyl)-propion-yl]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

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Reaction Steps

To an ice-cooled and stirred solution of 2-amino-3-benzoyl4,5,6,7-tetrahydrothieno[2,3-c]pyridine (0.775 mmol) in dry DMF (11 mL), was added BOC-Tyr-OH (0.08 mmol) and EDCl (0.08, 0.445 g) under an argon atmosphere. After stirring overnight, the mixture was evaporated under vacuum to give a solid residue, which was dissolved in a saturated sodium bicarbonate solution and is extracted with ethyl acetate (3×20 mL), then dried on magnesium sulfate. The organic layers were evaporated under vacuum to give a solid which is chromatographed on silica gel column eluting with ethyl acetate and petroleum ether to afford 2-amino-3-benzoyl-6-[2-t-butoxycarbonylamino-3-(4-hydroxyphenyl)-propion-yl]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine a yellow solid.

Provenance & Evidence