Citric Acid → HCID 54186349, compound

HRID 1602506Notes

Reaction equation

HRID 1602506 reaction equation
FC(F)(F)C(O)=O.[C:8]([C:12]1[N:13]=[C:14]([CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]([CH:54]=[CH:55][CH:56]=2)[C:23]([NH:25][C:26]2[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][S:44]([C:47]3[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=3)(=[O:46])=[O:45])[CH:38]=[CH:37][C:27]=2[O:28][CH2:29][C:30]([O:32]C(C)(C)C)=[O:31])=[O:24])[S:15][CH:16]=1)([CH3:11])([CH3:10])[CH3:9].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:8]([C:12]1[N:13]=[C:14]([CH2:17][CH2:18][O:19][C:20]2[CH:21]=[C:22]([CH:54]=[CH:55][CH:56]=2)[C:23]([NH:25][C:26]2[CH:40]=[C:39]([CH2:41][CH2:42][CH2:43][S:44]([C:47]3[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=3)(=[O:45])=[O:46])[CH:38]=[CH:37][C:27]=2[O:28][CH2:29][C:30]([OH:32])=[O:31])=[O:24])[S:15][CH:16]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 6422Trifluoroacetic acidHCID 54217389HCID 54217389, compound

Product 1

HCID 54186349HCID 54186349, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, trifluoroacetic acid (1.2 ml) was added to a mixture of tert-butyl 2-[3-[2-(4-tert-butyl-2-thiazolyl)ethoxy]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (185 mg, 0.25 mmol) and dichloromethane (2 ml), and the resulting reaction solution was stirred at room temperature for 3 hours and then concentrated under reduced pressure. Saturated sodium bicarbonate aqueous solution was added to the resulting residue and the product formed was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in water, and the solution obtained was adjusted to pH 2 by adding 10% citric acid aqueous solution. Thereafter, the solid material formed was collected by filtration and purified by silica gel column chromatography (eluent=chloroform:methanol=50:1) to give 2-[3-[2-(4-tert-butyl-2-thiazolyl)ethoxy]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid 0.5 hydrate (58 mg, 0.086 mmol, 34%).

Workup

  1. temperatureUnder ice-cooling
  2. customthe resulting reaction solution
  3. concentrationconcentrated under reduced pressure
  4. additionSaturated sodium bicarbonate aqueous solution was added to the resulting residue
  5. customthe product formed
  6. extractionwas extracted with ethyl acetate
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe resulting residue was dissolved in water
  11. customthe solution obtained
  12. customThereafter, the solid material formed
  13. filtrationwas collected by filtration
  14. custompurified by silica gel column chromatography (eluent=chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-7dc1d5fe3645489689bafbd51b01a269
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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