Triphenylphosphine → 5-(S)-Aminomethyl-3-[4'-tert-butoxycarbonyl-3'-fluorophenyl]-oxazolidine-2-one
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(CNC(CN2C3C(=CC=CC=3)C(C=O)=C2)=O)=CC=1.[N:42]([CH2:45][C@H:46]1[O:50][C:49](=[O:51])[N:48]([C:52]2[CH:57]=[CH:56][C:55]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])=[C:54]([F:65])[CH:53]=2)[CH2:47]1)=[N+]=[N-].C([BH3-])#N.[Na+]>O1CCCC1>[NH2:42][CH2:45][C@@H:46]1[O:50][C:49](=[O:51])[N:48]([C:52]2[CH:57]=[CH:56][C:55]([C:58]([O:60][C:61]([CH3:63])([CH3:62])[CH3:64])=[O:59])=[C:54]([F:65])[CH:53]=2)[CH2:47]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Triphenylphosphine (7.61 g, 29.0 mmol) was added to a mixture of BAL aldehyde resin (33.3 g, 9.67 mmol) and 5-(S)-azidomethyl-3-[4′-tert-butoxycarbonyl-3′-fluorophenyl]-oxazolidine-2-one (9.76 g, 29.0 mmol) in tetrahydrofuran (170 ml) under nitrogen at room temperature. The mixture was agitated at room temperature for 2 h and then at 75° C. for 16 h. The mixture was cooled to room temperature, and 1 M sodium cyanoborohydride in THF (58.0 ml, 58.0 mmol) was added in one portion. The reaction mixture was agitated for 8 h. The resulting amine resin was filtered, washed liberally with methanol and dichloromethane, and dried under vacuum.
Workup
- waitat 75° C. for 16 h
- temperatureThe mixture was cooled to room temperature
- stirringThe reaction mixture was agitated for 8 h
- filtrationThe resulting amine resin was filtered
- washwashed liberally with methanol and dichloromethane
- customdried under vacuum
Sources & evidence
- ORD record
- ord-e44ace312f9644b5a229a20be6373153
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562844B2
Reaction notes
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