Triphenylphosphine → (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide
Reaction equation
[C:1]1([CH2:7][C@H:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[C:1]1([CH2:7][C@H:8]([N:60]=[N+:61]=[N-:62])[C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Following the method of Itako et al. (Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 48(35), 1992, 7251-7264), a solution of (1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethanol (1.3 g, 6.3 mmol, from Reference Example 3) in tetrahydrofuran (60 mL) is cooled to 0° C. (ice-water bath). To the solution is added successively triphenylphosphine (1.8 g, 6.9 mmol), diethylazodicarboxylate (1.1 mL, 6.9 mmol), and diphenylphosphoryl azide (DPPA, 1.6 mL, 6.9 mmol). Following the addition of reagents, the reaction mixture is allowed to warm to room temperature and stir for 47 hours. Following this period, the mixture is concentrated under reduced pressure and purified by flash chromatography (silica gel, hexanes/toluene/diethyl ether) to give 1.2 g of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylazide as a pale blond oil contaminated with DPPA (detected by 1H NMR).
Workup
- additionthe addition of reagents
- waitFollowing this period
- concentrationthe mixture is concentrated under reduced pressure
- custompurified by flash chromatography (silica gel, hexanes/toluene/diethyl ether)
Sources & evidence
- ORD record
- ord-b438dc3fffec42a9adf66b796ec4c0e2
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07390910B2
Reaction notes
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