Hydrochloric Acid → Susalimod

HRID 743005Notes

Reaction equation

HRID 743005 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]3[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][N:26]=3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[K+].C(OCC)(=O)C.Cl>O.CC(C)=O>[OH:1][C:2]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([NH:24][C:25]3[C:30]([CH3:31])=[CH:29][CH:28]=[CH:27][N:26]=3)(=[O:23])=[O:22])=[CH:19][CH:20]=2)=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 19423387Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate

Product 1

HCID 3086668Susalimod

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Ethyl 2-hydroxy-5-[[4-[(3-methyl-2-pyridinylamino)sulfonyl]phenyl]ethynyl]benzoate (15.5 g, 35 mmol) was refluxed in potassium hydroxide (10 g, 0.15 mol) in water (100 ml) for 1 h. After cooling to ca 70° C., ethyl acetate (50 ml) was added and hydrochloric acid was added to reach pH 7-8. Cooling during stirring and then filration gave a solid that was disolved in acetone (100 ml) and water (100 ml). The solution was acidified at ca 50° C. and cooled, filtered and washed with water. Yield 8.0 g (56%).

Workup

  1. temperatureAfter cooling to ca 70° C.
  2. temperatureCooling
  3. customfilration gave a solid
  4. customwas acidified at ca 50° C.
  5. temperaturecooled
  6. filtrationfiltered
  7. washwashed with water

Sources & evidence

ORD record
ord-08ad6540f3074328b3dfa7cfdc1c2c8b
Source dataset
uspto-grants-1996_09
Patent number
US05556855

Reaction notes

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