Sodium Hydroxide → (S)-5-[Bis[2-(Boc-amino)ethyl]amino]-2-(Boc-amino)-5-oxopentanoic Acid

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Reaction Steps

To the solution of the ester (XV) (290 mg, 0.51 mmol) in MeOH (10 mL) was added 4 M NaOH dropwise until pH=13. The mixture was stirred overnight at room temperature before evaporating the MeOH under reduced pressure. The residue was mixed with water and washed with ether. After acidifying to pH˜3 with 2 M HCl, the product was extracted with DCM, dried over MgSO4 and concentrated under vacuum to give (S)-5-(bis(2-(tert-butoxycarbonylamino)ethyl)amino)-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid (XVI) (250 mg, 0.45 mmol, 88% yield). ESIMS found for C24H44N4O9 m/z 533 (M+H).

Provenance & Evidence