Sulfuric Acid → HCID 178499935, compound

HRID 1691969Notes

Reaction equation

HRID 1691969 reaction equation
[CH3:1][O:2][C:3](=[O:58])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12](=[O:26])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:15][C:14]=2[OH:25])[CH:9]=[CH:8][C:7]=1[O:27][CH2:28][C:29]1[CH:57]=[CH:56][C:32]2[C:33](=[O:55])[N:34](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[O:35][C:31]=2[CH:30]=1.C(C(C)=O)C(C)C.S(=O)(=O)(O)O.[OH-].[Na+]>O.CO>[CH3:1][O:2][C:3](=[O:58])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12](=[O:26])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:15][C:14]=2[OH:25])[CH:9]=[CH:8][C:7]=1[O:27][CH2:28][C:29]1[CH:57]=[CH:56][C:32]2[C:33]([OH:55])=[N:34][O:35][C:31]=2[CH:30]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7909Methyl Isobutyl KetoneHCID 14798Sodium HydroxideHCID 25064371HCID 25064371, compound

Product 1

HCID 178499935HCID 178499935, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

300 g of 3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-oxo-2-triphenylmethyl-2,3-dihydro-1,2-benzisoxazol-6-yl)methoxy]phenyl}propionic acid methyl ester was added to a mixture of 1200 mL of methyl isobutyl ketone and 600 mL of methanol. 43.5 mL of sulfuric acid was added dropwise under ice-cooling. This was stirred for 1 hour under water-cooled, and then stirred for 1 hour 30 minutes at room temperature. After adding 1200 mL of water and 200 mL of 20% sodium hydroxide aqueous solution, the result was stirred at room temperature for 30 minutes and solids were filtered to obtain 167 g of 3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl}propionic acid methyl ester in the form of a pale yellowish-white solid.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. stirringstirred for 1 hour 30 minutes at room temperature
  4. stirringthe result was stirred at room temperature for 30 minutes
  5. filtrationsolids were filtered

Sources & evidence

ORD record
ord-b743b996a31c4de2af75cf888f8dc701
Source dataset
uspto-grants-2012_04
Patent number
US08153816B2

Reaction notes

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