Benzylamine → Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine benzylamide

Participants

Reaction Conditions

Reaction Steps

3 (540 mg) was suspended in DMF (23 ml) and treated with benzylamine (0.374 ml), TEA (0.401 ml), NaHCO3 (solid) (924 mg) and sodium azide (117 mg). The suspension was cooled to -30° C., treated with DPPA (0.934 ml), and stirred at 0° C. for 72 hours. After removal of the DMF in vacuo, the residue was treated with 10% citric acid and extracted with EtOAc (3x). The combined extracts were washed with 10% citric acid (1x), H2O (1x), 10% NaHCO3 (aqueous) (1x), and brine (1x), dried over MgSO4, filtered and evaporated to dryness in vacuo to give a crude colorless oil (1.5 g). Flash chromatography on silica gel (90/10/1/1 of CH2Cl2 /MeOH/H2O/HOAc) gave 7 as a sticky foam (440 mg).

Provenance & Evidence