Water → HCID 10137557, compound

HRID 2308347Notes

Reaction equation

HRID 2308347 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:5]([NH:15][C:16](=[O:29])[CH:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH:4]=1)#[N:2].I[CH2:31][CH2:32][OH:33].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[OH:33][CH2:32][CH2:31][O:13][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[NH:15][C:16](=[O:29])[CH:17]([C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 10110685HCID 10110685, compound

Product 1

HCID 10137557HCID 10137557, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound prepared in Example 2(6) (150 mg) and 2-iodoethanol (100 mg) in DMF (2 ml), potassium carbonate (65 mg) was added under an atmosphere of argon. The mixture was stirred for overnight at room temperature. Water was added to the reaction mixture, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over and concentrated to give the crude crystal. The crude crystal was recrystallized with ethyl acetate/hexane to give the title compound (95 mg) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over and
  4. concentrationconcentrated
  5. customto give the crude crystal
  6. customThe crude crystal was recrystallized with ethyl acetate/hexane

Sources & evidence

ORD record
ord-b818fbaefb274a539f169f798b957971
Source dataset
uspto-grants-2004_12
Patent number
US06835752B2

Reaction notes

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