Pyridine → N-[(5-Fluoro-2-nitrophenyl)carbamoyl]glycine methyl ester
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH:12]=1)C(N=[N+]=[N-])=O.Cl.[CH3:17][O:18][C:19](=[O:22])[CH2:20][NH2:21].[N:23]1[CH:28]=CC=CC=1.C(OCC)(=[O:31])C>C1(C)C=CC=CC=1.O>[CH3:17][O:18][C:19](=[O:22])[CH2:20][NH:21][C:28](=[O:31])[NH:23][C:6]1[CH:12]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:13]([O-:15])=[O:14]Participants
Procedure
A solution of 5-fluoro-2-nitrobenzoyl azide (5.46 g, 0.026 mol) in toluene is stirred at 65° C. for 90 minutes, cooled, treated with glycine methyl ester hydrochloride (3.63 g, 0.029 mol), stirred for 10 minutes, treated with pyridine (5 mL, 0.062 mol), stirred overnight, diluted with water and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 0.4M hydrochloric acid and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a solid. The solid is slurried in an ether/hexanes (6:4) solution, filtered and dried to give a yellow solid. Column chromatography of the yellow solid using silica gel and ethyl acetate in hexanes solutions gives the title product as a yellow solid, mp 133.2°-135.3° C.
Workup
- temperaturecooled
- stirringstirred overnight
- extractionextracted with ethyl acetate
- washwashed sequentially with water, 0.4M hydrochloric acid and brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated in vacuo
- customto obtain a solid
- filtrationfiltered
- customdried
- customto give a yellow solid
Sources & evidence
- ORD record
- ord-69a2b4c2526d4d5398640616d859013f
- Source dataset
- uspto-grants-1997_02
- Patent number
- US05604180
Reaction notes
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