Chloride → HCID 178473384, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound G (1.0 g, 1.8 mmol) in THF (7 mL) was added 3.1N aqueous NaOH (4.0 mL) and stirred for 5 min. The reaction mixture was cooled to ˜5° C., and then a solution of tripsyl chloride added drop wise (2.2 g, 7.3 mmol) in THF (5 mL) and stirred at room temperature overnight (˜18 h). The reaction mixture was diluted with H2O (130 mL), acidified with 2% H2SO4 (15 mL) and extracted with EtOAc (3×80 mL). Organic layer were combined and washed with H2O (2×400 mL), saturated NaHCO3 (100 mL), H2O (200 mL) and brine (200 mL). The organic layer was separated dried over MgSO4 and solvent removed in vacuo to afford (2.9 g) of crude product. This was purified by normal phase flash chromatography (5-10% MeOH/DCM) to afford compound H (0.52 g, 1.0 mmol). LC-MS [M+H] 833.8 (C41H64N6O8S2+H, calc: 834.1).

Provenance & Evidence