Acetonitrile → 278598-83-7

HRID 984752Notes

Reaction equation

HRID 984752 reaction equation
[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([NH:24][C:25](=[O:43])[C@@H:26]([NH:31][C:32](=[O:42])[CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:41])[CH2:27][CH:28]([CH3:30])[CH3:29])[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1)=[O:3].C(=O)([O-])[O-].[K+:48].[K+].C(#N)C>CO.O>[K+:48].[NH2:1][C:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([NH:24][C:25](=[O:43])[C@@H:26]([NH:31][C:32](=[O:42])[CH2:33][O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:41])[CH2:27][CH:28]([CH3:30])[CH3:29])[C:21]([O-:23])=[O:22])=[CH:15][CH:14]=2)=[O:11])[CH2:6][CH2:5]1)=[O:3]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 9809516278598-52-0

Product 1

HCID 23697549278598-83-7Yield 199.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of Example 27 (10 g) in methanol (150 ml) was warmed to reflux to obtain a clear solution. To this was added a solution of potassium carbonate (1.16 g) in water (7.5 ml). After heating under reflux for two minutes the solvents were evaporated in vacuo to give a crisp foam. To this was added acetonitrile (100 ml) and the mixture was warmed to reflux, during which time the foam collapsed and started to crystallise. After ten minutes the mixture was allowed to cool to 20° C. then filtered under reduced pressure, washed with acetonitrile (25 ml) and ether (50 ml) to give the title compound as a white solid (10.65 g, 100%). The product is believed to be isolated in the form of its monohydrate. Solubility in water: >250 mg/ml.

Workup

  1. temperatureto reflux
  2. customto obtain a clear solution
  3. temperatureAfter heating
  4. temperatureunder reflux for two minutes the solvents
  5. customwere evaporated in vacuo
  6. customto give a crisp foam
  7. temperaturethe mixture was warmed
  8. temperatureto reflux, during which time the foam
  9. customto crystallise
  10. waitAfter ten minutes the mixture was allowed
  11. filtrationthen filtered under reduced pressure
  12. washwashed with acetonitrile (25 ml) and ether (50 ml)

Sources & evidence

ORD record
ord-5456b91ee02d447dbb27ea817f4da6ed
Source dataset
uspto-grants-2005_03
Patent number
US06867192B1

Reaction notes

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