HCID 23594053, compound → HCID 23594052, compound

HRID 434072Notes

Reaction equation

HRID 434072 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH3:2].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH3:2][CH2:1][O:3][C:4]([CH:5]1[C:9]([OH:11])([CH3:10])[CH2:8][CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:19]

Participants

4

Reactant 2

HCID 23594053HCID 23594053, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23594052HCID 23594052, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 27A (5 g, 18.29 mmol) in toluene (100 mL) cooled at 0° C. was added solid potassium tert-butoxide (2.05 g, 18.29 mmol) in small portions to maintain the solution temperature <5° C. The reaction was stirred at 0° C. for 45 min, then quenched by addition of ice-cooled 10% aqueous KHSO4 solution and extracted with CH2Cl2 (3×). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a brown oily residue, which was chromatographed (silica gel) eluting with EtOAc/hexane (1:3) to give 530 mg of the title compound (racemate).

Workup

  1. temperatureto maintain the solution temperature <5° C
  2. customquenched by addition of ice-
  3. temperaturecooled 10% aqueous KHSO4 solution
  4. extractionextracted with CH2Cl2 (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto give a brown oily residue, which
  10. customwas chromatographed (silica gel)
  11. washeluting with EtOAc/hexane (1:3)

Sources & evidence

ORD record
ord-025546353cdf463bbb97299c2fcb7ce1
Source dataset
uspto-grants-2003_12
Patent number
US06670386B2

Reaction notes

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