Sulfuric acid magnesium salt (1:1) → 3-Azido-N-cyclopropyl-2-hydroxyhexanamide

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Reaction Conditions

Reaction Steps

A flask equipped with an overhead stirrer, thermometer and reflux condenser was placed under a nitrogen atmosphere then charged with compound 38 (20.0 g, 118 mmol), sodium azide (NaN3; 31.0 g, 473 mmol), magnesium sulfate (MgSO4; 14.0 g, 118 mmol) and methanol (MeOH; 200 mL). The mixture was heated to 65±5° C. for 2 hours then cooled to 25±5° C. and filtered through a pad of Celite 545. The solvent was removed under reduced pressure resulting in a thick oil which was taken up in IPAc (250 mL) then washed with water (3×250 mL). The organic phase was dried over sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to provide compound 40 as a white solid. 1H NMR (500 MHz, d6-DMSO) 7.87 (s, 1H), 5.97 (d, J=6.0, 1H), 4.02 (dt, J=6.0, 3.8 Hz, 1H), 2.70-2.65 (m, 1H), 1.60-1.20 (m, 4H), 0.88 (t, J=7.0 Hz, 3H), 0.63-0.58 (m, 2H), 0.51-0.46 (m, 2H).

Provenance & Evidence