Hydrochloric Acid → HCID 66668795, compound

HRID 1618021Notes

Reaction equation

HRID 1618021 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=3)=[O:20])=[CH:13][CH:12]=2)=[N:9][N:10]=1)C.C(=O)([O-])O.[Na+].Cl>C(O)C.O>[CH3:27][C:23]1[CH:22]=[C:21]([C:19](=[O:20])[CH2:18][CH:17]([C:14]2[CH:15]=[CH:16][C:11]([C:8]3[O:7][C:6]([CH2:5][C:4]([OH:35])=[O:3])=[N:10][N:9]=3)=[CH:12][CH:13]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66668306HCID 66668306, compound

Product 1

HCID 66668795HCID 66668795, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (5-{4-[(−)-3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-phenyl}-[1,3,4]oxadiazol-2-yl)-acetic acid ethyl ester (146 mg) in a mixture of ethanol (5 mL) and water (1.25 mL) was added sodium hydrogencarbonate (104 mg) and the reaction mixture stirred at room temperature for 4 h. The solution was adjusted to approximately pH 3 by using 1 M aqueous hydrochloric acid and then extracted over a sat. solution of brine (50 mL) with ethyl acetate (3×50 mL). The combined organic phases were dried over sodium sulfate and the crude reaction product purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of dichloromethane:methanol (100:0 to 90:10). Light yellow solid. MS (ESI+): m/z=442.4 ([M+H]+).

Workup

  1. extractionextracted over a sat. solution of brine (50 mL) with ethyl acetate (3×50 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customthe crude reaction product
  4. custompurified by silica gel chromatography
  5. washeluting with a gradient of dichloromethane:methanol (100:0 to 90:10)

Sources & evidence

ORD record
ord-74ff5db7545d4088afff109e4d00eb4e
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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