4-Nitrophenol → L-Serine

Participants

Reaction Steps

2-Benzyloxybenzoic acid 4 was then reacted with p-nitrophenol 5 and dicyclohexylcarbodiimide (DCC) in ethyl acetate to produce, after work-up, 4-nitrophenyl-2-(benzyloxy)benzoate 6 in 45% yield. Treatment of the benzoate 6 with L-serine 7 and triethylamine (TEA) in tetrahydrofuran (THF)/water gave the protected E/D fragment 8 of Exochelin 786SM(R) in 79% yield. This segment undergoes subsequent reaction with a protected form of the C/F fragment to generate the largest subunit of the target compound.

Provenance & Evidence