Water → (R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one
Reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C@@H:24]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:25]Br)=[C:17]2[C:22]=1[NH:21][C:20](=[O:23])[CH:19]=[CH:18]2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>CN(C=O)C>[N:1]([CH2:25][C@@H:24]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:23])[NH:21]2)[O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])=[N+:2]=[N-:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
NaN3 (266 mg, 4.1 mmol) was added to a stirred solution of (R)-8-(benzyloxy)-5-[2-bromo-1-[(tert-butyldimethylsilyl)oxy]ethyl]quinolin-2(1H)-one (1 g, 2.05 mmol) in DMF (20 mL) at rt and warmed to 80° C. for 3 h. The resulting solution was poured into H2O (80 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (2×100 mL), brine (100 mL), dried over Na2SO4 (s), and concentrated to give the title compound (1.37 g) as a yellow solid. The compound was used with no further purification. ES/MS calcd. for C24H31N4O3Si+ 451.2. found m/z=451.3 (M+H)+.
Workup
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with H2O (2×100 mL), brine (100 mL)
- dry with materialdried over Na2SO4 (s)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a5776904d3504a0d9793882497d659b0
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367829B2
Reaction notes
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