Flurbiprofen → 1-Phenethylamine, (-)-

HRID 1449782Notes

Reaction equation

[CH3:1][CH:2]([C:16]([OH:18])=[O:17])[C:3]1[CH:4]=[CH:5][C:6]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:7]([F:9])[CH:8]=1.[CH3:19][C@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C[C@H](C(O)=O)C1C=CC(C2C=CC=CC=2)=C(F)C=1.[CH3:46][C@H:47]([NH2:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CO.C1(C)C=CC=CC=1>[CH3:19][C@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:1][CH:2]([C:16]([OH:18])=[O:17])[C:3]1[CH:4]=[CH:5][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:7]([F:9])[CH:8]=1.[CH3:46][C@H:47]([NH2:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Racemic flurbiprofen (61.0 g) was dissolved in a mixture of methanol (40 ml) and toluene (160 ml). The mixture was heated to 60° C. and (S)-α-methylbenzylamine 16.9 ml was added over 10 minutes. A seed crystal of (S)-flurbiprofen-(S)-α-methylbenzylamine was added to the reaction mixture which was then cooled to 0° to 5° C., and held at that temperature for one hour. The precipitate was collected by filtration to give a (S)-α-methylbenzylamine salt of (S)-enriched flurbiprofen-(S)-α-methylbenzylamine of an enantiomeric purity of 92.2%. After recrystallisation of the precipitate from a mixture of methanol (48 ml) and toluene (192 ml), a further-(S)-enriched-flurbiprofen-(S)-α-methylbenzylamine of an enantiomeric purity of 98.5% was obtained.

Workup

temperaturewas then cooled to 0° to 5° C.
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-8f68159783184737b8f0a3486921b1a9
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05599969

Reaction notes

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