Acetonitrile → Acetonitrile

HRID 625902Notes

Reaction equation

HRID 625902 reaction equation
[CH3:1][C@@H:2]([NH:12][CH2:13][C@H:14]([OH:25])[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([NH:22][CH:23]=[O:24])[CH:16]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[C@H:26]([OH:35])([C:32]([OH:34])=[O:33])[C@@H:27]([OH:31])[C:28]([OH:30])=[O:29].[C:36](#[N:38])[CH3:37]>CO>[CH3:1][C@@H:2]([NH:12][CH2:13][C@H:14]([OH:25])[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([NH:22][CH:23]=[O:24])[CH:16]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[C:28]([C@@H:27]([C@H:26]([C:32]([O-:34])=[O:33])[OH:35])[OH:31])([O-:30])=[O:29].[C:36](#[N:38])[CH3:37]

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 9827062Arformoterol tartrate

Product 2

HCID 6342AcetonitrileYield 75%HCID 86649829HCID 86649829, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of 348.8 mg (0.70 mmol) of (R,R)-arformoterol tartrate Form B in 15 mL of methanol was heated to the reflux temperature of the solvent for 15 minutes or until a clear yellow solution was obtained. Afterwards, it was cooled to about 60-50° C. and followed by addition of 5 mL aliquots of acetonitrile (total of 45 mL) at the same temperature until a suspension was obtained. The suspension was further cooled to 10-40° C. and stirred at this temperature for 10 minutes. The product was collected by filtration, washed with acetonitrile and dried under vacuum (2 mbar, equivalent to 1.5 mm Hg) at 40° C. for 12 hours to provide 262.4 mg (75% yield) of acetonitrile solvate of (R,R)-Formoterol-L-tartrate, which contained acetonitrile in a range between 2 and 4% (w/w), as determined by 1H-NMR or TGA analysis.

Workup

  1. temperaturewas heated to the reflux temperature of the solvent for 15 minutes or until a clear yellow solution
  2. customwas obtained
  3. customwas obtained
  4. temperatureThe suspension was further cooled to 10-40° C.
  5. filtrationThe product was collected by filtration
  6. washwashed with acetonitrile
  7. customdried under vacuum (2 mbar, equivalent to 1.5 mm Hg) at 40° C. for 12 hours

Sources & evidence

ORD record
ord-9c38bc0f0c4d458e8d2f5cf19535c7f4
Source dataset
uspto-grants-2016_04
Patent number
US09309186B2

Reaction notes

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