Methanol → Acetonitrile

HRID 625904Notes

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].CO>C(#N)C>[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:2](#[N:12])[CH3:1]

Participants

Conditions

Temperature: 55 °C

Procedure

A suspension of 407.3 mg (0.82 mmol) of (R,R)-arformoterol tartrate Form B and 15 mL of methanol was heated to the reflux temperature of the solvent for 15 min. Then, the solution obtained was allowed to cool to about 50-60° C., followed by addition of 45 mL of acetonitrile at the same temperature. Afterwards, the solution was cooled to room temperature and stirred for 30 minutes. The product was collected by filtration, washed with acetonitrile and dried under vacuum (2-3 mbar, equivalent to 1.5-2.25 mm Hg) at 60° C. for 2 hours to provide 345.5 mg (85% yield) of acetonitrile solvate of (R,R)-Formoterol-L-tartrate, which contained about 1.6% (w/w) of acetonitrile, as determined by TGA analysis.

Workup

temperaturewas heated to the reflux temperature of the solvent for 15 min
customThen, the solution obtained
temperatureAfterwards, the solution was cooled to room temperature
filtrationThe product was collected by filtration
washwashed with acetonitrile
customdried under vacuum (2-3 mbar, equivalent to 1.5-2.25 mm Hg) at 60° C. for 2 hours

Sources & evidence

ORD record: ord-772ed5f6787443ce9e390b1ddd334b90
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309186B2

Reaction notes

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