Triphenylphosphine → S-(2-((1S,4S)-4-((tert-butoxycarbonyl)amino)-1-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)cyclopent-2-en-1-yl)ethyl) ethanethioate

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Reaction Steps

To a solution of the product of Example 1, Step D (1950 mg, 3.98 mmol, 1 eq) in THF (40 mL) at rt under Ar was added triphenylphosphine (2.09 g, 7.96 mmol, 2 eq), diisopropylazodicarboxylate (1.55 mL, 7.96 mmol, 2 eq) and thioacetic acid (0.59 mL, 7.96 mmol, 2 eq). After 2 hr, water and saturated NaHCO3 were added, the aqueous was extracted with ether, the organics combined, dried over MgSO4 and concentrated. Purification by chromatography (80 g column) eluting with 30 to 60% EtOAc/heptane afforded the product of Step A. 1H NMR (CHLOROFORM-d) δ: 8.71 (s, 1H), 7.71 (s, 1H), 6.21 (dd, J=5.6, 1.7 Hz, 1H), 5.80 (dd, J=5.6, 2.0 Hz, 1H), 4.75-4.94 (m, 3H), 4.64-4.75 (m, 1H), 3.96-4.07 (m, 1H), 3.86-3.96 (m, 1H), 3.14 (t, J=5.7 Hz, 2H), 2.69-2.79 (m, 2H), 2.65 (dd, J=13.4, 8.1 Hz, 1H), 2.27 (s, 3H), 1.95-2.13 (m, 2H), 1.81-1.94 (m, 1H), 1.44 (s, 9H). Calculated for C24H30F3N3O4S: 536.2 (M+23). found: 536.2.

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