Diisopropylethylamine → (S)-2-hydroxy-N-[(S)-6-oxo-5-(2,2,2-trifluoro-ethyl)-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-propionamide

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Reaction Steps

A solution of 0.26 g (0.85 mmol) (S)-7-amino-5-(2,2,2-trifluoro-ethyl)-5H,7H-dibenzo[b,d]azepin-6-one in 18 ml tetrahydrofurane was treated at 0° C. with 0.08 g (0.94 mmol) L-lactic acid, 0.13 g (0.85 mmol) 1-hydroxybenzotriazole hydrate, 297 μl (1.70 mmol) N-ethyldiisopropylamine and 0.17 g (0.85 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochlorid. After stirring at room temperature overnight the mixture was extracted with 1N aqueous hydrochloric acid/ethylacetate. Purification by chromatography on silicagel with ethylacetate/heptane (0-100/100-0) yielded 0.22 g (68%) (S)-2-hydroxy-N—[(S)-6-oxo-5-(2,2,2-trifluoro-ethyl)-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-propionamide as grey solid, MS: m/e: 379.4 (M+H+), [α] 589=−23° (1.1% in CHCl3).

Provenance & Evidence