Morpholine → 1-[[Methyl[(S)-3-[(4-morpholinylcarbonyl)amino]-2-oxo-4-phenylbutyl]amino]carbonyl]-L-proline, phenylmethyl ester

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Reaction Steps

Morpholine (1 ml., 11.4 mmole) is added to a stirring solution of 1-[[[(S)-3-[[(4-nitrophenoxy)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester (0.9 g., 1.58 mmole) in toluene at 0° in one portion. The reaction mixture turns yellow in 15 minutes and TLC indicates complete loss of starting material after 30 minutes. The resulting solution is washed sequentially with water, 1N hydrochloric acid, and 10% sodium bicarbonate. The organic layer is dried (MgSO4) and concentrated. The crude product is purified by preparative layer chromatography to give 0.26 g. of 1-[[methyl[(S)-3-[(4-morpholinylcarbonyl)amino]carbonyl]-2-oxo-4-phenylbutyl]amino]carbonyl]-L-proline, phenylmethyl ester as a yellow oil. TLC (ethyl acetate) Rf =0.18.

Provenance & Evidence