Water → HCID 22097565, compound

HRID 1458890Notes

Reaction equation

HRID 1458890 reaction equation
COC([C@H:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12](OC)=[O:13])[CH2:7][C@H:6]1[C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=O.CC(C)([O-])C.[K+].O>C1(C)C=CC=CC=1>[CH2:18]([N:17]([CH2:20][CH3:21])[C:16]([CH:6]1[CH:5]2[CH2:10][CH2:9][N:8]([CH2:11][C:12]2=[O:13])[CH2:7]1)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 131720466HCID 131720466, compound

Product 1

HCID 22097565HCID 22097565, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 12 (159 g, 0.503 mole) in toluene (700 ml) was added dropwise over a period 2.5 hours to a solution of potassium t-butoxide (169 g, 1.51 mole) in toluene (1.9L) at 110° C. under a nitrogen condition. The mixture was heated at reflux for 1 hour and cooled down to room temperature. Water (400 ml) was added then the layers were heated at reflux for 2 hours. After the organic layer was separated, the aqueous layer was neutralized and extracted with EtOAc for 15 hours with continuous extraction apparatus. The combined extracts were dried over MgSO4 and concentrated down. Recrystallization from EtOH gave 13 (34.6 g, 31%) as a colorless crystal. The stereochemistry was determined by X-Ray analysis, 13C and NMR.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe layers were heated
  4. temperatureat reflux for 2 hours
  5. customAfter the organic layer was separated
  6. extractionextracted with EtOAc for 15 hours with continuous extraction apparatus
  7. dry with materialThe combined extracts were dried over MgSO4
  8. concentrationconcentrated down
  9. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-20768954e4934bc78984b6d5834c3236
Source dataset
uspto-grants-1998_12
Patent number
US05852038

Reaction notes

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