Ethyl phenylacetate → ethyl 7-(N-t-butoxycarbonylamino)-3-oxo-2-phenylheptanoate

Participants

Reaction Steps

The target compound was prepared as a pale yellow oil in an amount 7.8 g at a yield of 48.1% in the same manner as in Example 1 except that 10 g (45.8 mmol) of 5-(N-t-butoxycarbonylamino)pentanoic acid instead of 5-(N-benzyloxycarbonylamino)pentanoic acid was dissolved in 70 ml of THF and 11.1 g (68.7 mmol) of CDI was added; 9.5 ml (72 mmol) of diisopropylamine and 40 ml of THF were added and 42 ml (69 mmol) of 1.63N BA solution was added dropwise; 10.6 g (68.7 mmol) of ethyl phenylacetate instead of methyl phenylacetate was dissolved in 20 ml of THF; and 30 ml of saturated aqueous ammonium chloride solution was added to the reaction solution, the reaction was terminated, 70 g of 4N hydrochloric acid was added, and 100 ml of ethylacetate was further added. The analytical results on the target compound are given below.

Provenance & Evidence