Hydrochloric Acid → HCID 178447588, compound

HRID 501780Notes

Reaction equation

HRID 501780 reaction equation
[C:1]([O:7][CH2:8][O:9][C:10](=[O:49])[CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([C:19](=[O:33])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:22][C:21]=2[OH:32])[CH:16]=[CH:15][C:14]=1[O:34][CH2:35][C:36]1[CH:48]=[CH:47][C:39]2[C:40]([O:43]COC)=[N:41][O:42][C:38]=2[CH:37]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl.O.[OH-].[Na+]>O1CCOCC1.CO.C(OCC)(=O)C>[C:1]([O:7][CH2:8][O:9][C:10](=[O:49])[CH2:11][CH2:12][C:13]1[CH:18]=[C:17]([C:19](=[O:33])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)=[CH:22][C:21]=2[OH:32])[CH:16]=[CH:15][C:14]=1[O:34][CH2:35][C:36]1[CH:48]=[CH:47][C:39]2[C:40]([OH:43])=[N:41][O:42][C:38]=2[CH:37]=1)(=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68457984HCID 68457984, compound

Product 1

HCID 178447588HCID 178447588, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1.02 g of {[3-(5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-{[3-(methoxymethoxy)-1,2-benzisoxazol-6-yl]methoxy}phenyl) propanoyl]oxy}methyl pivalate was dissolved in 8 mL of 1,4-dioxane and 8 mL of methanol, to which 6 mL of 6M hydrochloric acid was added at room temperature, and this mixture was stirred for 50 minutes at the same temperature. The reaction mixture, to which water was added, was adjusted to pH 7 with an aqueous solution of sodium hydroxide, and then ethyl acetate was added to this mixture and the organic phase was separated therefrom. The remaining aqueous phase was extracted with ethyl acetate, and organic phases were combined together. After the resultant organic phase was washed with a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue, to which a mixture of hexane and ethyl acetate [3:1] was added, was filtered out to yield 0.56 g of [(3-{5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl} propanoyl)oxy]methyl pivalate as white solid.

Workup

  1. customthe organic phase was separated
  2. extractionThe remaining aqueous phase was extracted with ethyl acetate, and organic phases
  3. washAfter the resultant organic phase was washed with a saturated sodium chloride solution
  4. dry with materialthe washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. additionThe resultant residue, to which a mixture of hexane and ethyl acetate [3:1]
  7. additionwas added
  8. filtrationwas filtered out

Sources & evidence

ORD record
ord-a89867fae65e454e854eb1fe8a4cd9fd
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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