4-Nitrophenol → HCID 129844758, compound

Participants

Reaction Steps

Scheme 5 shows the synthesis of compound 8, in which the promoiety is inserted in between Boc-alanine and a trytophan residue. This is achieved by first reacting 1-chloromethyl- chloroformate 2 with p-nitrophenol in the presence of N-methyl morpholine to yield 3. Substitution of chloride in 1-chloromethyl p-nitrophenol carbonate 3 with iodide is accomplished by reacting 3 with sodium iodide to give 1-iodomethyl p-nitrophenol carbonate (4) in quantitative yield. This iodo compound 4 is reacted with the cesium salt of Boc-alanine to yield Boc-alanineoxymethyl-p-nitrophenol carbonate 6.

Provenance & Evidence