Acetic Acid → HCID 11698244, compound

Participants

Reaction Steps

A mixture of Example 552A (0.546 g, 2.5 mmol) in dimethylacetamide (14 mL) was treated with Dess-Martin periodinane (8.25 mL of 15 wt % solution in CH2Cl2, 2.1 mmol) stirred for 15 minutes, and filtered. The filtrate was added to a solution of Example 552C (1.005 g, 2.79 mmol) in CH2Cl2/methanol (11 mL) and the resulting mixture was treated with acetic acid (1.65 mL) and macroporous polystyrene bound cyanoborohydride resin (3.3 g, 7.5 mmol), shaken at 70° C. for 15 hours, filtered, concentrated, and purified by flash chromatography eluting with 30% ethyl acetate/hexanes. The purified product was dissolved in CH2Cl2 (100 mL), treated with TFA (20 mL), stirred for 1.5 hours, and concentrated to provide the desired product. MS (DCI) m/e 444 (M+H)+.

Provenance & Evidence