Ethyl 4-methoxybut-2-ynoate → (S)-2-(4-tert-Butyl-phenoxymethyl)-5-methoxymethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

Participants

Reaction Steps

To a solution of (S)-5-(4-tert-butyl-phenoxymethyl)-4,5-dihydro-oxazol-2-yl-amine (2.3 g, 9.26 mmol) (prepared according to the procedures employed in Step 1 through 2 of Example 1) in ethanol (35 mL) was added 1.7 g (12.04 mmol) of 4-methoxy-but-2-ynoic acid ethyl ester (prepared in accordance with the procedures as described in Larock, J Org Chem 2002, 67, 9318). This mixture was stirred at reflux for 6 hours and cooled. The reaction mixture was concentrated and loaded onto a silica gel column. Chromatography with 1-10% EtOH/CH2Cl2 provided 2.22 g of the title compound. [α]D25 −18.00 (c 0.5, CHCl3)

Provenance & Evidence