Water → HCID 57563615, compound

HRID 1726321Notes

Reaction equation

HRID 1726321 reaction equation
[O:1]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([NH2:19])=O)=[C:11]([C:20](=[O:34])[NH:21][CH:22]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:23][CH:24]([CH3:26])[CH3:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O>O1CCOCC1>[CH3:25][CH:24]([CH3:26])[CH2:23][CH:22]([NH:21][C:20](=[O:34])[C:11]1[CH:10]=[C:9]([CH2:8][O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[CH:13][C:12]=1[CH2:15][CH2:16][C:17]#[N:19])[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 57563477HCID 57563477, compound

Product 1

HCID 57563615HCID 57563615, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of the compound prepared in Example 15 (119 mg) in dioxane (2 ml) were added pyridine (0.1 ml) and trifluoromethanesulfonic acid anhydride (54 μl) at 0° C. under an atmosphere of argon. The mixture was stirred at room temperature for 10 minutes. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with n-hexane:ethyl acetate to give the title compound (94 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 subsequently, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with n-hexane

Sources & evidence

ORD record
ord-34c9d4398b884cdc92c07039fdf7ff51
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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