Triphenylphosphine → 5-(S)-Aminomethyl-3-[4'-dimethoxymethyl-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]([CH:58]([O:61][CH3:62])[O:59][CH3:60])=[C:54]([F:63])[CH:53]=2)[CH2:47]1)=[N+]=[N-].C([BH3-])#N.[Na+]>C1COCC1>[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]([CH:58]([O:59][CH3:60])[O:61][CH3:62])=[C:54]([F:63])[CH:53]=2)[CH2:47]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Triphenylphosphine (0.130 g, 0.496 mmol) was added to a mixture of BAL aldehyde resin (0.57 g, 0.165 mmol) and 5-(S)-azidomethyl-3-[4′-dimethoxymethyl-3′-fluorophenyl]-oxazolidine-2-one (0.154 g, 0.496 mmol) in THF (3 ml) at room temperature. The mixture was stirred 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 (0.99 ml, 0.992 mmol) was added in one portion. The reaction mixture was agitated for 8 h. The resulting amine resin was 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
- washThe resulting amine resin was washed liberally with methanol and dichloromethane
- customdried under vacuum
Sources & evidence
- ORD record
- ord-60a459e8f36348028e53bab934d14d01
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562844B2
Reaction notes
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