Hydrochloric Acid → 2-(3-Bromophenyl)-2-((tert-butoxycarbonyl)(methyl)amino)acetic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:22]I.[Cl-].[Na+].Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:22])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (3-bromo-phenyl)-tert-butoxycarbonylamino-acetic acid (490 mg, 1.49 mmol) in THF (10 mL) at room temperature was added sodium hydride (125 mg, 60% inmineral oil, 3.1 mmol) and the resulting pale yellow suspension was stirred at room temperature for 3 hours. Methyl iodide (528 mg, 3.7 mmol) was added and the resulting mixture was stirred overnight. Satuated sodium chloride (10 mL) was added and the aqueous phase pH was adjusted to 5 by addition of 1 N hydrochloric acid. The resulting mixture was extracted with ethyl acetate (10 mL×3) and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified using a gradient of methanol in dichloromethane to afford (3-bromo-phenyl)-(tert-butoxy-carbonyl-methyl-amino)-acetic acid (390 mg, 76%) as an oil. MS: m/z 344 (M+H+).
Workup
- stirringthe resulting mixture was stirred overnight
- extractionThe resulting mixture was extracted with ethyl acetate (10 mL×3)
- dry with materialthe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified
Sources & evidence
- ORD record
- ord-0ed4a25c0e3844a0bec8badbee67d829
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242280B2
Reaction notes
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