Methanol → HCID 86649829, compound

HRID 625903Notes

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]

Participants

Conditions

Temperature: 55 °C

Procedure

A suspension of 135 mg (0.27 mmol) of (R,R)-arformoterol tartrate Form A and 7.5 mL of methanol was heated to the reflux temperature of the solvent for 10 min. Then, the solution obtained was allowed to cool to about 50-60° C., followed by addition of 19 mL of acetonitrile at the same temperature. Afterwards, the solution was cooled to room temperature and stirred for 1 hour. 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 25° C. for 1 hour to provide acetonitrile solvate of (R,R)-Formoterol-L-tartrate, which contained about 2.5% (w/w) of acetonitrile, as determined by 1H-NMR analysis.

Workup

temperaturewas heated to the reflux temperature of the solvent for 10 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 25° C. for 1 hour

Sources & evidence

ORD record: ord-2b3e07d9203f4e52a4cabf9851886b6f
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309186B2

Reaction notes

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