Hydrochloric Acid → HCID 178525321, compound

HRID 909406Notes

Reaction equation

HRID 909406 reaction equation
C[O:2][C:3](=[O:39])[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:38]=[CH:37][C:32]2[C:33]([OH:36])=[N:34][O:35][C:31]=2[CH:30]=1.O.[OH-].[Na+].Cl>CO>[CH:20]1([O:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([C:10]3[CH:9]=[CH:8][C:7]([O:27][CH2:28][C:29]4[CH:38]=[CH:37][C:32]5[C:33]([OH:36])=[N:34][O:35][C:31]=5[CH:30]=4)=[C:6]([CH2:5][CH2:4][C:3]([OH:39])=[O:2])[CH:11]=3)=[O:26])=[C:14]([OH:25])[CH:15]=2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 178499935HCID 178499935, compound

Product 1

HCID 178525321HCID 178525321, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 182 mL of methanol, 26.0 g of 3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl}propionic acid methyl ester was suspended. After dropping 78 mL of water of 10.5 g of sodium hydroxide at room temperature, the result was stirred for 30 minutes at the same temperature. The reaction mixture was added to water. After adjusting to pH 1.5 with a 6 mol/L hydrochloric acid, solids were filtered. The obtained solids were dissolved in a mixture solution of chloroform and methanol. After washing with water, solvent was distilled off under reduced pressure to obtain 22.5 g of 3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl}propionic acid in the form of a light yellowish solid.

Workup

  1. customat room temperature
  2. filtrationwere filtered
  3. dissolutionThe obtained solids were dissolved in a mixture solution of chloroform and methanol
  4. washAfter washing with water, solvent
  5. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-4c0ddc900d8c4d2f9cb6dcb17adb36e6
Source dataset
uspto-grants-2011_09
Patent number
US08017789B2

Reaction notes

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