Ethyl Acetate → HCID 69199559, compound

HRID 2116622Notes

Reaction equation

HRID 2116622 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].C[O-].[Na+].[CH2:17]1[O:20][C@@H:18]1[CH3:19].[C:21](OCC)(=O)C>CO.[Cl-].[NH4+].CCCCCC>[CH2:1]([O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH2:17][C@H:18]([OH:20])[CH3:19])=[CH:7][CH:6]=1)=[O:4])[CH3:21]

Participants

8

Reactant 4

HCID 8857Ethyl Acetate2×HCID 146261(R)-1,2-EpoxypropaneHCID 286535methyl 1H-indazole-6-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 69199559HCID 69199559, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 8058HexaneSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of the product from Step A (3.5 g, 19.8 mmol) in methanol (30 mL) was added a sodium methoxide solution in methanol (25%, 9.2 ml, 29.3 mmol) at room temperature. After 30 min, (R)-propylene oxide (2.8 mL, 39.6 mmol) was added, and the resultant solution stirred for 3 h. The solution was diluted with saturated aqueous solution of ammonium chloride (20 mL) and extracted with ethyl acetate (3×65 mL). The combined extract was washed with brine (10 mL), dried (MgSO4) and evaporated to give a residue which was subjected to chromatography (silica, 30% ethyl acetate in hexane to 50% ethyl acetate in hexane) to give an oil (1.8 g, 39%): MS (ES) m/z 235 (M+); 1H NMR (CDCl3) 8.20 (1H, s), 8.07 (1H, s), 7.84 1H, d, J=7.2 Hz), 7.81 (1H, d, J=7.2 Hz), 4.47 (2H, dd, J=7.2 Hz), 4.34 (2H, m), 3.20 (1H, m), 1.44 (3H, t, J=7.2 Hz). 1.31 (3H, d, J=6.4 Hz).

Workup

  1. extractionextracted with ethyl acetate (3×65 mL)
  2. extractionThe combined extract
  3. washwas washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a residue which

Sources & evidence

ORD record
ord-56698cc576b44d33a688bae73ded043f
Source dataset
uspto-grants-2008_10
Patent number
US07439262B1

Reaction notes

Loading…