4-Methylmorpholine → N-(tert-Butoxycarbonyl)-2,6-dimethyl-L-tyrosyl-N-{(2R)-2-[(benzyloxycarbonyl)amino]-3-phenylpropyl}-D-alaninamide

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Reaction Steps

Benzyl-[(1R)-2-(D-alanylamino)-1-benzylethyl]carbamate (145 mg, 0.41 mmol) was combined with N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosine (described in BioOrg. Med. Chem. Letts, 2003, p 599; 129 mg, 0.41 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride salt (94 mg, 0.49 mmol), 1-hydroxybenzotriazole monohydrate (69 mg, 0.45 mmol) and N-methylmorpholine (42 mg, 0.41 mmol) in DMF (5 mL) at room temperature under a nitrogen atmosphere. The mixture was stirred at room temperature for 16 h and then diluted with 10 mL of EtOAc and washed with 10 mL of a 10% aqueous solution of citric acid, 10 mL of water, 10 mL of a 3% aqueous solution of sodium bicarbonate, and finally 10 mL of a saturated aqueous brine solution. The organic layer was dried over sodium sulfate and evaporated under reduced pressure to give 243 mg (92%) of a white foam of the title compound, which was used with no further purification.

Provenance & Evidence