Sodium Chloride → HCID 86747370, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve [1R,2S,3R,4S,5R]-2-[[(1,1-dimethylethoxy)carbonyl][(4-methoxyphenyl)methyl]amino]-β-hydroxy-3,4,5-tris(phenylmethoxy)-cyclopentanepropanoic acid, ethyl ester (2.018 g, 2.73 mmol) in a 4:1 mixture of acetonitrile/water (75 mL) and cool to 0° C. with an ice bath. Add ceric ammonium nitrate (4.23 g, 7.72 mmol) and stir for 1 hour. Pour into a mixture of water/ethyl acetate containing sodium chloride, separate the organic phase, wash with dilute sodium hydrogen carbonate and aqueous sodium chloride. Dry (MgSO4), evaporate the solvent in vacuo and subject to Kugelrohr distillation to remove p-methoxybenzaldehyde (94° C. @ high vacuum) to give the title compound remaining as a white solid which is recrystallized from cyclohexane.

Provenance & Evidence