Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1.[N:25]([C@H:28]([C:32]1[CH:37]=[C:36]([F:38])[C:35]([F:39])=[C:34]([F:40])[CH:33]=1)[C@@H:29]([OH:31])[CH3:30])=[N+]=[N-].[C:41]([O:45][C:46](=O)[O:47]C(C)(C)C)([CH3:44])([CH3:43])[CH3:42]>O>[C:41]([O:45][C:46](=[O:47])[NH:25][C@H:28]([C:32]1[CH:37]=[C:36]([F:38])[C:35]([F:39])=[C:34]([F:40])[CH:33]=1)[C@@H:29]([OH:31])[CH3:30])([CH3:44])([CH3:43])[CH3:42]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In nitrogen atmosphere, triphenylphosphine (5.85 g) was added to a THF solution (75 mL) of (1R,2S)-1-azido-1-(3,4,5-trifluorophenyl)propan-2-ol (5.16 g). This reaction solution was stirred at room temperature for 10 min, then water (5 mL) was added the reaction solution. This mixture was stirred at 60° C. for 3.5 hr. The reaction solution was cooled to room temperature, and then di-tert-butylcarbonate (5.35 g) was added to the reaction solution. The resulting reaction solution was stirred at room temperature for 45 min and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=9:1) to give 5.88 g of the title compound. The physical property values of this compound were as follows:
Workup
- stirringThis mixture was stirred at 60° C. for 3.5 hr
- temperatureThe reaction solution was cooled to room temperature
- customThe resulting reaction solution
- stirringwas stirred at room temperature for 45 min
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (toluene:ethyl acetate=9:1)
Sources & evidence
- ORD record
- ord-9b929db65e1f4d39ba38def4d69f12d7
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737141B2
Linked notes
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