Ammonia → tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

HRID 1350204Notes

Reaction equation

[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24]OS(C3C=CC(C)=CC=3)(=O)=O)[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:36]>C1COCC1.CCOC(C)=O>[NH2:36][CH2:24][C:21]1[N:20]=[C:19]([C@H:10]([CH2:9][CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:23][N:22]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A soluton of tert-butyl(3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,2,4-oxadiazol-5-yl]hexanoate (preparation 177) (1.2 g, 2.37 mmol) in THF (40 ml) was treated with concentrated ammonia solution and heated in a bomb at 40° C. for 18 hours. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3 solution followed by brine. The organic extract was dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The colourless oil was purified on a silica column eluting with a solvent gradient of pentane:EtOAc (4:1) gradually changing to (1:1) and then changing to DCM:MeOH:NH3 (95:5:0.5) to afford the title compound as a colourless oil (782 mg, 94%).

Workup

washwashed with sat. NaHCO3 solution
extractionThe organic extract
dry with materialwas dried over anhydrous MgSO4
filtrationfiltered
customthe solvent removed under reduced pressure
customThe colourless oil was purified on a silica column
washeluting with a solvent gradient of pentane:EtOAc (4:1)

Sources & evidence

ORD record: ord-447e5dc0b6164fdc9bfc28568f0f7e09
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214694B2

Reaction notes

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