2,2-Dimethoxypropane → HCID 59396014, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1,1-dimethylethyl (2-{[(1S)-1-(hydroxymethyl)-3-buten-1-yl]amino}-2-oxoethyl)carbamate D21 (37 g) in toluene (370 ml) stirred at 25° C. were added 2,2-bis(methyloxy)propane (370 ml, 3020 mmol) and p-toluenesulfonic acid monohydrate (3.7 g, 19.45 mmol). The reaction mixture was stirred at reflux (85° C. internal, oil bath 105° C.) for 1.5 hour (clear solution). The check by TLC (DCM/MeOH 95/5) showed the reaction to be completed. The solvent was evaporated to obtain a brown oil that was chromatographed (Biotage 75 L, silica, eluting with Cy/EtOAc 8/2, 7/3) to give the title compound D22 (30 g) as yellow oil. UPLC (Acid GEN_QC): rt=0.69 minutes, peak observed: 299 (M+1). C15H26N2O4 requires 298. 1H NMR (400 MHz, CDCl3) δ ppm 1.46 (s, 9 H) 1.54 (s, 3 H) 1.67 (s, 3 H) 2.30-2.49 (m, 2 H) 3.71-4.05 (m, 5 H) 5.04-5.22 (m, 2 H) 5.37-5.52 (m, 1 H) 5.65-5.81 (m, 1 H)

Provenance & Evidence