Sodium Hydroxide → HCID 67454510, compound

Participants

Reaction Conditions

Reaction Steps

The product of step (b) (132 mg, 0.334 mmol, 1.00 equiv) and NaOH (2.5 N, 0.5 mL) were dissolved in methanol (2 mL) and heated to 60° C. in a sealed tube for three hours. The reaction mixture was diluted with water (˜50 mL) and EtOAc (˜50 mL), stirred, and separated. The aqueous layer was adjusted to pH 1 with 2N HCl and extracted with EtOAc. The organic layer was concentrated en vacuo and the residue (39 mg, 0.102 mmol, 1 equiv) was dissolved in DMF (5 mL). PS-carbodiimide resin (140 mg, 0.153 mmol, 1.5 equiv) was added and the reaction was stirred at room temperature for 18 hours. The reaction mixture was filtered and washed twice alternately with methanol and methylene chloride. The filtrate was concentrated en vacuo and the residue was purified by silica gel column (0-10% MeOH in CH2Cl2). The residue was triturated with CH2Cl2/Hexane to give 4 mg of the title compound as a beige powder (11%). MS (ES+) m/e 364 [M+H]+

Provenance & Evidence