tert-Butanol → HCID 86711936, compound

HRID 1475244Notes

Reaction equation

HRID 1475244 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][N:10]2[C:14]([CH3:15])=[N:13][C:12]([C:16]3[O:20][N:19]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=4)[N:17]=3)=[N:11]2)[CH:6]=CC=1)=C.C[N+]1([O-])CC[O:36]CC1.C[C:41]([OH:44])([CH3:43])[CH3:42]>O.O=[Os](=O)(=O)=O>[CH3:15][C:14]1[N:10]([CH2:9][C:5]2[CH:6]=[C:42]([CH:41]([OH:44])[CH2:43][OH:36])[CH:1]=[CH:3][CH:4]=2)[N:11]=[C:12]([C:16]2[O:20][N:19]=[C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[N:17]=2)[N:13]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 86711935HCID 86711935, compound

Product 1

HCID 86711936HCID 86711936, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

To a solution of 5-(5-methyl-1-(3-vinylbenzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (Example 84; 110 mg, 0.26 mmol) in t-BuOH (5 mL), were added N-methylmorpholine-N-oxide (152 mg, 1.3 mmol) and OsO4 (10 mg, 0.04 mmol). The reaction mixture was stirred at RT for 24 h, diluted with H2O (20 mL) and extracted with EtOAc (2×10 mL). The combined organic layers were washed with H2O (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure; the residue was purified by prep-HPLC (10% to 40% MeCN/H2O containing 0.1% trifluoroacetic acid) to give the title compound as a white solid; MS (ES+) C21H18F3N5O4 requires: 461. found: 462 [M+H]+; 1H-NMR (500 MHz, DMSO-d6) δ 8.23 (d, J=8.5 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.33-7.30 (m, 3H), 7.17 (d, J=7 Hz, 1H), 5.56 (s, 2H), 4.54-4.51 (m, 1H), 3.44-3.40 (m, 4H), 2.57 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organic layers were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by prep-HPLC (10% to 40% MeCN/H2O containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-cd6f57ae29a543d5bcb43fb025f940cd
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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