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

HRID 540978

Reaction equation

[CH:1]1([NH:4][C:5]([CH:7]2[CH:9]([CH2:10][CH2:11][CH3:12])[O:8]2)=[O:6])[CH2:3][CH2:2]1.[N-:13]=[N+:14]=[N-:15].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CO>[N:13]([CH:9]([CH2:10][CH2:11][CH3:12])[CH:7]([OH:8])[C:5]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:6])=[N+:14]=[N-:15]

Participants

Conditions

Temperature: 65 °C

Procedure

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).

Workup

customA flask equipped with an overhead stirrer
temperaturethermometer and reflux condenser
temperaturethen cooled to 25±5° C.
filtrationfiltered through a pad of Celite 545
customThe solvent was removed under reduced pressure
customresulting in a thick oil which
washthen washed with water (3×250 mL)
dry with materialThe organic phase was dried over sodium sulfate (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-f8094360c09548f5a95833db17110297
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871904B2

Linked notes

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