Water → ((6S,8S)-6-(Anilinocarbonyl)-3-{[(benzyloxy)carbonyl][3-(trifluoromethyl)benzyl]amino}-8-methyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-8-yl)acetic acid

Participants

Reaction Steps

To a solution of 117a (1.073 g, 1.740 mmol) in 15.4 mL CH3CN/CCl4/H2O (2:2:3), were added NaIO4 (1.56 g, 7.31 mmol) and a solution of RuCl3.H2O (18 mg, 0.087 mmol) in 2.25 mL of CH3CN/CCl4/H2O (2:2:3). The mixture was stirred vigorously for 16 h, then was poured into H2O and extracted with CH2Cl2 (2×). The combined organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to afford 1.17 g of 117b as a brown foam, which was used in the following step without further purification. MS (ESI) 657.3 (M+Na+); 633.4 (M−H+).

Provenance & Evidence