Ethyl bromoacetate → 3-[2-Azido-2-(2-ethoxycarbonylmethoxyethoxy)ethoxy]benzoic acid
Reaction equation
[N:1]([CH:4]([O:16][CH2:17][CH2:18][OH:19])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[N+:2]=[N-:3].[H-].[Na+].[CH2:22]([O:24][C:25](=[O:28])[CH2:26]Br)[CH3:23]>C1COCC1>[N:1]([CH:4]([O:16][CH2:17][CH2:18][O:19][CH2:26][C:25]([O:24][CH2:22][CH3:23])=[O:28])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[N+:2]=[N-:3]Participants
Procedure
To a solution of 3-[2-azido-2-(2-hydroxy-ethoxy)-ethoxy]-benzoic acid (0.535 g, 2 mmol) in dry THF (6 ml) was added NaH (60% dispersion, 0.246 g, 6 mmol) at 0° C. After 10 minutes, ethyl-2-bromoacetate (0.488 ml, 4.4 mmol) was added. The reaction was then warmed up to room temperature and stirred for 4 hours. The reaction was quenched by pouring it into ice-cold water (50 ml). The mixture was extracted with DCM (2×50 ml) and the DCM extracts were discarded. The aqueous layer was then acidified to pH 2 with 1 N HCl, and extracted with DCM (2×50 ml). These DCM extracts were combined, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by column chromatography (1×20 cm). The title compound, eluted with 2% methanol in DCM, was obtained as an oil (0.223 g, 31.6%). ES-MS, m/z 351.95 (M−1).
Workup
- customThe reaction was quenched
- additionby pouring it into ice-cold water (50 ml)
- extractionThe mixture was extracted with DCM (2×50 ml)
- extractionextracted with DCM (2×50 ml)
- dry with materialdried over MgSO4
- customevaporated under reduced pressure
- customThe residue was purified by column chromatography (1×20 cm)
- washThe title compound, eluted with 2% methanol in DCM
Sources & evidence
- ORD record
- ord-30b81a7863dc4d3998e7b65f983d3020
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414116B2
Reaction notes
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