Sodium Hydroxide → HCID 54045798, compound

HRID 977840Notes

Reaction equation

HRID 977840 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C@H:15]([O:25]C(=O)C2C=CC=CC=2)[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:9][C:8]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C@H:15]([OH:25])[CH2:16][CH2:17][CH2:18][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)=[CH:9][C:8]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54487833HCID 54487833, compound

Product 1

HCID 54045798HCID 54045798, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 ml of a 1N aqueous solution of sodium hydroxide were added to a solution of 460 mg (0.70 mmol) of (R)-N-[2-t-butyl-5-(6-cyclohexyl-3-benzoyloxyhexyl)phenyl]-2-(9H-xanthen-9-yl)acetamide [prepared as described in step (i) above] in 40 ml of ethanol, and the resulting mixture was heated under reflux for 2 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure, and the residue was first diluted with ethyl acetate and then acidified with 2N aqueous hydrochloric acid. The organic phase was separated and then washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The mixture was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was recrystallized from diisopropyl ether, to give 180 mg (yield 47%) of the title compound as crystals, melting at 128°-129° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  4. additionthe residue was first diluted with ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  7. dry with materialThe mixture was dried over anhydrous sodium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. customThe resulting residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-9ed9e5aa8d0a48a5916c2416e611d4fd
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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