Potassium Carbonate → HCID 89955656, compound

HRID 705372Notes

Reaction equation

HRID 705372 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:27]=[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[C:25]([CH:33]4[CH2:35][CH2:34]4)=[CH:24][C:18]=3[C:19]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]3[CH:27]=[C:26]([N:28]([CH2:42][C:41]4[CH:44]=[CH:45][C:38]([O:37][CH3:36])=[CH:39][CH:40]=4)[S:29]([CH3:32])(=[O:30])=[O:31])[C:25]([CH:33]4[CH2:35][CH2:34]4)=[CH:24][C:18]=3[C:19]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 67981740HCID 67981740, compound

Product 1

HCID 89955656HCID 89955656, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 18G (4.0 g, 8.14 mmol), 4-methoxybenzyl bromide 2.21 g, 11 mmol) and potassium carbonate (1.35 g, 9.76 mmol) in N,N-dimethylformamide (25 mL) under N2 was heated at 50° C. for 2 hours, cooled and concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated brine, dried (MgSO4), filtered and concentrated. The solid was triturated in hexanes and the solid was collected by filtration and dried to give the title compound as a white solid (4.49 g, 90% yield). MS (ESI+) m/z 612 (M+H)+.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe solid was triturated in hexanes
  9. filtrationthe solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-4ebb7aa129d94025a43255288a5bc4a7
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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