Sodium Hydroxide → HCID 21110693, compound

HRID 1766691Notes

Reaction equation

HRID 1766691 reaction equation
[OH:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]([CH3:25])=[CH:9][C:10]([NH:16][C:17](=[O:24])[CH2:18][C:19]([O:21]CC)=[O:20])=[C:11]3[C:15]=2[CH2:14][CH2:13][CH2:12]3)=[CH:4][C:3]=1[CH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[OH-].[Na+]>CO>[OH:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]([CH3:25])=[CH:9][C:10]([NH:16][C:17](=[O:24])[CH2:18][C:19]([OH:21])=[O:20])=[C:11]3[C:15]=2[CH2:14][CH2:13][CH2:12]3)=[CH:4][C:3]=1[CH2:28][CH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23031228HCID 23031228, compound

Product 1

HCID 21110693HCID 21110693, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl N-{7-[4-hydroxy-3-(tetrahydropyran-4-ylmethyl)phenoxy]-6-methylindan-4-yl}malonamate (50 mg) were added methanol (10 mL) and a 1 mol/L aqueous solution of sodium hydroxide (8 mL), and the mixture was stirred under an argon atmosphere at 50° C. for 30 min. Adding water (20 mL), the reaction mixture was washed with diethyl ether (10 mL) twice. Adding 1 mol/L hydrochloric acid (20 mL) and brine (10 mL), the aqueous layer was extracted with ethyl acetate (10 mL) twice. The organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to dryness to give the title compound (45 mg).

Workup

  1. washAdding water (20 mL), the reaction mixture was washed with diethyl ether (10 mL) twice
  2. additionAdding 1 mol/L hydrochloric acid (20 mL) and brine (10 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (10 mL) twice
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure to dryness

Sources & evidence

ORD record
ord-ec31da049fb444ba9358d7d8f8261447
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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