Sodium hydride → HCID 19419198, compound

HRID 864495Notes

Reaction equation

HRID 864495 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:8])[CH2:6]Br.[F:9][C:10]([F:33])([F:32])[C:11]1[CH:12]=[C:13]([CH2:21][O:22][CH2:23][CH:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[OH:25])[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=1>CN(C)C=O>[F:9][C:10]([F:32])([F:33])[C:11]1[CH:12]=[C:13]([CH2:21][O:22][CH2:23][CH:24]([O:25][CH2:6][C:5]([O:4][CH3:3])=[O:8])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:14]=[C:15]([C:17]([F:19])([F:20])[F:18])[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 19957508HCID 19957508, compound

Product 1

HCID 19419198HCID 19419198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Sodium hydride (25 mg, 60%) was added to a stirred solution of methylbromoacetate (84 mg) and the compound of Example 3 (200 mg) in dry dimethylformamide (0.5 ml). The mixture was stirred at 23° C. for 18 hrs, then partitioned between water and ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 9:1 hexanes:ethyl acetate to give the title compound as a clear oil. 1H NMR (250MHz, CDCl3) δ3.60-3.68 (1H, m), 3.68 (3H, s), 3.80-3.94 (1H, m), 3.95-4.21 (2H, q), 4.64-4.80 (3H, m), 7.23-7.39 (5H, m), 7.80 (3H, s).

Workup

  1. custompartitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with 9:1 hexanes

Sources & evidence

ORD record
ord-f22c5d4440b740ffa061f35ea6ef608d
Source dataset
uspto-grants-1996_10
Patent number
US05563161

Reaction notes

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