Tris(hydroxymethyl)aminomethane → N-[(1S,2S,4R)-1-Benzyl-4-(3,3-dimethylbutylcarbamoyl)-2-hydroxypentyl]-3-(2-oxopyrrolidin-1-yl)-5-phenylbenzamide

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Reaction Steps

Polystyrene linked carbodiimide (21 mg, 1.7 mmol/g, 0.036 mmol) was placed in a vial with DCM (1 ml). To this was added HOBT (5 mg, 0.036 mmol) in 1 ml DCM/DMF=4:1, 5-(2-oxo-pyrrolidin-1-yl)-biphenyl-3-carboxylic acid (D11) (10 mg, 0.036 mmol) in 1 ml DCM/DMF=4:1, and (2R,4S,5S)-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid (3,3-dimethylbutyl)amide (D2) (in 1 ml DCM). The mixture was stirred at room temperature overnight. Scavenger resins trisamine (˜100 mg) and isocyanate (˜100 mg) were added and the mixture was stirred for another 1.5 hours. The resins were filtered and the solvent evaporated in vacuo. Column chromatography on silica gel (5% MeOH in DCM) gave E6 (5 mg).

Provenance & Evidence