(-)-Mandelic acid → trans-(1r,2s)-2-(3,4-Difluorophenyl)cyclopropanaminium (2r)-2-hydroxy-2-phenylethanoate

HRID 603322Notes

Reaction equation

[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([OH:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.[CH2:12]1[C@@H:14]([NH2:15])[C@@H:13]1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1>C(OCC)(=O)C>[CH2:12]1[C@@H:14]([NH3+:15])[C@H:13]1[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=1.[CH:1]1[CH:2]=[CH:3][C:4]([CH:7]([OH:11])[C:8]([O-:10])=[O:9])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 25 °C

Procedure

R-(−)-Mandelic acid (2.26 kg) was added to a solution containing trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropylamine (2.6 kg, 91.8% enantiomeric excess), stirring at 17° C. in ethyl acetate (45.3 L). The mixture was stirred at 25° C. for 3 hours and 8 minutes, then filtered and washed twice with ethyl acetate (13.8 kg total). The crystalline product was dried at 40° C. under reduced pressure for 23 hours, affording trans-(1R,2S)-2-(3,4-difluorophenyl)cyclopropanaminium (2R)-2-hydroxy-2-phenylethanoate (4.45 kg).

Workup

filtrationfiltered
washwashed twice with ethyl acetate (13.8 kg total)
customThe crystalline product was dried at 40° C. under reduced pressure for 23 hours

Sources & evidence

ORD record: ord-df504a26877b4f9fa4aad1f6565050a6
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906662B2

Reaction notes

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