4-Methylmorpholine → HCID 19366850, compound

Participants

Reaction Steps

Part G: A solution of 3.4 g (10 mmol) of 2-hydroxy-4-[(3-phenoxybenzyl)sulfonyl]butanoic acid from Part F and 2.1 g (15 mM) HOBT in 15 mL of anhydrous DMF was cooled in an ice bath and treated with 2.3 g (12 mM) of EDC. After 2 hours, the reaction was treated with a solution of 1.5 g (12 mM) of 4-(2-aminoethyl)morpholine and 3.3 mL (3.1 g, 30 mM) of N-methylmorpholine in 5 mL anhydrous DMF. After stirring for 66 hours, the reaction was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with saturated sodium bicarbonate solution and brine, dried over MgSO4, and concentrated to yield 3.5 g of crude product. The crude product was chromatographed on silica gel using 5% methanol/ethyl acetate followed by 20% ethanol/THF to yield 2.1 g of N1-(2-morpholinoethyl)-2-hydroxy-4-[(3-phenoxybenzyl)sulfonyl]butanamide suitable for the next reaction.

Provenance & Evidence