Sodium Hydroxide → HCID 59714839, compound

HRID 2223908Notes

Reaction equation

HRID 2223908 reaction equation
[C:1]1([CH3:46])[CH:6]=[CH:5][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][CH2:30][O:31][C:32]4[CH:33]=[C:34]([C:42]([O:44]C)=[O:43])[CH:35]=[C:36]([CH:41]=4)[C:37]([O:39]C)=[O:38])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([CH3:46])[CH:2]=[CH:3][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][CH2:30][O:31][C:32]4[CH:41]=[C:36]([C:37]([OH:39])=[O:38])[CH:35]=[C:34]([CH:33]=4)[C:42]([OH:44])=[O:43])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59714930HCID 59714930, compound

Product 1

HCID 59714839HCID 59714839, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of dimethyl 5-[2-[1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]ethoxy]isophthalate (synthesized in Example 28) (255 mg) dissolved in methanol (5 mL) was added a 2N aqueous sodium hydroxide solution (2.0 mL). The solution was stirred at room temperature for 24 hours. The reaction solution was concentrated under reduced pressure. Water was then added to the solution, and it was neutralized with acetic acid (0.23 mL) and extracted with chloroform-ethanol (80:20). The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated under reduced pressure to give the title compound (243 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionWater was then added to the solution, and it
  3. extractionextracted with chloroform-ethanol (80:20)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-8fd1a508ad0a48de938f1e58c418121d
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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