Sodium Thiosulfate → Morpholine-4-carboxylic acid {(s)-1-[(s)-1-(3-cyclopropyl-1,2,4-oxadiazole-5-carbonyl)-propylcarbamoyl]-3,3-difluoro-hexyl}-amide

To a solution of morpholine-4-carboxylic acid (1-{1-[(3-cyclopropyl-[1,2,4]oxadiazol-5-yl)-hydroxy-methyl]-propylcarbamoyl}-3,3-difluoro-hexyl)-amide (145 mg, 0.31 mmol) in dry dichloromethane (3 mL) under N2 is added Dess-Martin periodinane (15% wt solution in dichloromethane, 1.73 g, 0.061 mmol). The reaction is stirred at room temperature for 2 hr, then quenched with a solution of Na2S2O3 193 mg, 1.22 mmol) in saturated NaHCO3 (30 mL). The aqueous layer is extracted with dichloromethane (2×30 mL). The organic layers are dried over magnesium sulfate and concentrated in vacuum. The residue is purified over 12 g silica gel, eluted with ethyl acetate: heptane (1:1 then 2:1) to afford the desired ketone (119 mg, 81%) as a solid.

1. extractionThe aqueous layer is extracted with dichloromethane (2×30 mL)
2. dry with materialThe organic layers are dried over magnesium sulfate
3. concentrationconcentrated in vacuum
4. customThe residue is purified over 12 g silica gel
5. washeluted with ethyl acetate: heptane (1:1

ORD record

ord-b7e49a47dd6d4330a0912887488764a3

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07482448B2