Imidazole → HCID 15286443, compound

Participants

Reaction Steps

To a solution of (2R)-2-hydroxypropanoic acid (5 g) in DMF (20 ml) was added TBDPSCl (33.0 g) and imidazole (16.4 g). The reaction was then stirred overnight at RT. The reaction was partitioned between EtOAc (200 ml) and H2O (200 ml). The organics were recovered and washed with 10% citric acid (200 ml), H2O (200 ml) and finally brine (200 ml). The organics were then collected, dried (MgSO4) before being reduced in vacuo. The residue was dissolved in MeOH (200 ml), cooled in an ice bath and potassium carbonate (6.9 g) in H2O was added. After stirring at room temperature for 6 h the solvent was removed in vacuo and the residue diluted with H2O (100 ml). The pH was then adjusted to pH 4 with 10% citric acid, and the aqueous extracted three times with EtOAc (3×200 ml). The organics were collected dried MgSO4 before reducing in vacuo to give the subtitle compound as a colourless oil. Yield: 7.5 g

Provenance & Evidence