Acetone → HCID 178491209, compound

HRID 1913952Notes

Reaction equation

HRID 1913952 reaction equation
C(OC([NH:8][CH:9]([CH2:38][C:39]1[C:44]([CH3:45])=[CH:43][C:42]([C:46](=[O:48])[NH2:47])=[CH:41][C:40]=1[CH3:49])[C:10]([N:12]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:36][CH3:37])=[C:31]([CH:35]=1)[C:32]([OH:34])=[O:33])[CH:13]([C:15]1[NH:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:19]=1)[CH3:14])=[O:11])=O)(C)(C)C.CC(C)=O.Cl.[OH-].[Na+]>O>[NH2:8][CH:9]([CH2:38][C:39]1[C:44]([CH3:45])=[CH:43][C:42]([C:46](=[O:48])[NH2:47])=[CH:41][C:40]=1[CH3:49])[C:10]([N:12]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:36][CH3:37])=[C:31]([CH:35]=1)[C:32]([OH:34])=[O:33])[CH:13]([C:15]1[NH:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:19]=1)[CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178491186HCID 178491186, compound

Product 1

HCID 178491209HCID 178491209, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A 1 L three-necked round-bottomed flask equipped with a mechanical stirrer, addition funnel and a thermocouple was charged without agitation. 34.2 g of 5-({[2-tert-butoxycarbonylamino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionyl]-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-amino}-methyl)-2-methoxy-benzoic acid (see Example 9 of US 2005/0203143), 340 ml of acetone, and 17 ml of 204 mmolar concentrated HCl were combined in the flask. The stirring was started and the resulting slurry formed a clear solution. This solution was heated to 45° C. under vigorous stirring and aged at this temperature for a period of two hours. After the completion, the reaction mass was cooled to ambient temperature and the supernatant was removed by suction. The vessel along with the residue was rinsed with 20 ml of acetone and then removed as previously. 170 ml of water was added and the reaction mass and was aged under stirring until a homogeneus solution resulted. This solution was then added over a period of ˜½ hr to a solution of 90 ml of 1N NaOH and water. The pH was adjusted to 6.5-7.0 accordingly. The resulting slurry was aged for about 2 hrs at ambient temperature, cooled to 10-15° C., aged at that temperature for about 1 hr, and then filtered. The solid was washed with 10 ml water, air-dried for a period of 4 to 5 hrs, and then placed in a vacuum oven at 50-55° C. until the water content was less than 3%.

Workup

  1. customA 1 L three-necked round-bottomed flask equipped with a mechanical stirrer, addition funnel
  2. additiona thermocouple was charged without agitation
  3. customthe resulting slurry formed a clear solution
  4. temperatureAfter the completion, the reaction mass was cooled to ambient temperature
  5. customthe supernatant was removed by suction
  6. washThe vessel along with the residue was rinsed with 20 ml of acetone
  7. customremoved as previously
  8. addition170 ml of water was added
  9. stirringunder stirring until a homogeneus solution
  10. customresulted
  11. waitThe resulting slurry was aged for about 2 hrs at ambient temperature
  12. temperaturecooled to 10-15° C.
  13. waitaged at that temperature for about 1 hr
  14. filtrationfiltered
  15. washThe solid was washed with 10 ml water
  16. customair-dried for a period of 4 to 5 hrs
  17. customplaced in a vacuum oven at 50-55° C. until the water content

Sources & evidence

ORD record
ord-6dc47f2383614a96a576cadfffb25113
Source dataset
uspto-grants-2013_12
Patent number
US08609865B2

Reaction notes

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