1,1-Dimethylethyl (2E,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-(phenylthio)-2-pentenoate → HCID 11638423, compound

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Reaction Steps

A mixture of Example 480A (5 g, 13.2 mmol) and Wilkinson's catalyst (1 g) in tolune (125 mL) was stirred under H2 at 60° C. for 18 hours, cooled, filtered through silica gel, and concentrated. The concentrate was dissolved in 3:1:1 THF/water/MeOH (150 mL), treated with with a 10-fold excess of LiOH, and stirred for 24 hrs. The mixture was poured into saturated NaH2PO4 (200 mL) and extracted three times with ethyl acetate (200 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 324, 326 (M−H)−, (M+H)+.

Provenance & Evidence