Water → HCID 59707355, compound

HRID 1881375Notes

Reaction equation

HRID 1881375 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([OH:22])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23](Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>C1COCC1.C(OCC)(=O)C>[CH2:23]([O:22][C:14]1[CH:13]=[C:12]([O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 59103876HCID 59103876, compound

Product 1

HCID 59707355HCID 59707355, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (1) (1.07 g, 3.44 mmol) and benzyl chloride (0.43 mL, 3.78 mmol) in THF (100 mL) was added potassium carbonate (1.57 g, 11 mmol), then the reaction was heated to 90° C. for 18 h. After cooling to room temperature, water (200 mL) and ethyl acetate (200 mL) were added; the organic layer was separated and washed with water (2×200 mL), dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The crude product was purified by silcagel column chromatography eluting with a gradient from 10%-50% ethyl acetate in hexane. Fractions containing the pure desired product were combined and solvent was removed under reduced pressure to produce a colorless oil (890 mg, 64%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe organic layer was separated
  3. washwashed with water (2×200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe crude product was purified by silcagel column chromatography
  8. washeluting with a gradient from 10%-50% ethyl acetate in hexane
  9. additionFractions containing the pure desired product
  10. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d6d43f854740495691ee6ac47b147861
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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