Oxolane--water (1/1) → HCID 86623619, compound

HRID 1820999Notes

Reaction equation

HRID 1820999 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]([OH:25])CO)=[CH:18][C:17]=3[CH3:26])[N:12]=2)=[CH:7][C:6]=1[C:27]([F:30])([F:29])[F:28])([CH3:3])[CH3:2].I([O-])(=O)(=O)=O.[Na+].C1COCC1.O>[Cl-].[Na+].O>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]=[O:25])=[CH:18][C:17]=3[CH3:26])[N:12]=2)=[CH:7][C:6]=1[C:27]([F:28])([F:29])[F:30])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 21881883Oxolane--water (1/1)HCID 23667635Sodium periodateHCID 68888983HCID 68888983, compound

Product 1

HCID 86623619HCID 86623619, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 49 mg (0.12 mmol) of 1-(4-(5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)ethane-1,2-diol and 37 mg (0.17 mmol) of sodium periodate in 9 mL of 2:1 v:v THF/H2O mix solvent. After stirring at rt for 4 h, the mixture was poured into brine and extracted with EtOAc (3×10 mL). Organic layers were combined, dried over MgSO4, and concentrated. Chromatography on Biotage 40S cartridge using 1:9 v/v EtOAc/hexanes as the eluant afforded 40 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=5.9, 6H), 2.78 (s, 3H), 4.79 (m, 1H), 7.16 (d, J=9.0, 1H), 7.84-7.86 (m, 2H), 8.28 (d, J=8.5, 1H), 8.32 (dd, J=2.2, 8.9, 1H), 8.44 (d, J=2.1, 1H), 10.09 (s, 1H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cf1ffdbdf35f4d95afbf0e6dd14cda94
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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