Potassium Carbonate → HCID 178450826, compound

HRID 1355601Notes

Reaction equation

HRID 1355601 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([CH2:11][NH2:12])=[CH:9][CH:10]=1)=[NH:4].[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>O1CCOCC1.O>[OH:1][NH:2][C:3]([C:5]1[C:6]([C:13]([O:14][C:5]([CH3:6])([CH3:10])[CH3:3])=[O:16])=[N:7][C:8]([CH2:11][NH2:12])=[CH:9][CH:10]=1)=[NH:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 178513313HCID 178513313, compound

Product 1

HCID 178450826HCID 178450826, compoundYield 107.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product of Example 53 (11-5) (0.5 g, 3.01 mmol) in dioxane and water (6 ml each) was added potassium carbonate (832 mg, 6.02 mmol), followed by Boc-anhydride (0.66 g, 3.01 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated and the remaining residue was dissolved in ethylacetate and washed with sodium bicarbonate (saturated) and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash column chromatography in 8/2 ethylacetate/hexanes followed by ethylacetate and 9/1 dichloromethane/methanol afforded 0.43 g product as a white solid. NMR δ (ppm) CDCl3: 8.8 (d, 1H), 7.9 (dd, 1H), 7.3 (d, 1H), 6.6 (bs, 1H), 5.5 (bs, 1H), 4.8 (bs, 1H), 4.4 (d, 2H), 1.4 (s, 9H)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe remaining residue was dissolved in ethylacetate
  3. washwashed with sodium bicarbonate (saturated) and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-597a3eb24a5c4433bc42f2e0ee1e92d5
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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