Ethanolamine → HCID 43389001, compound
Reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:34][CH2:35][CH2:36][OH:37].[Br:38][C:39]1[O:43][C:42]([C:44]([OH:46])=O)=[CH:41][CH:40]=1>ClCCl>[Br:38][C:39]1[O:43][C:42]([C:44]([NH:34][CH2:35][CH2:36][OH:37])=[O:46])=[CH:41][CH:40]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.66 g, 1.7 mmol), N,N-diisopropylethylamine (0.82 mL, 4.7 mmol) and 2-aminoethanol (0.14 mL, 2.4 mmol) were added to a solution of 5-bromo-2-furoic acid (0.30 g, 1.6 mmol) in dichloromethane (15 mL), and the mixture was stirred at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, water (5 mL) was added thereto. The whole was extracted with ethyl acetate (10 mL), and the organic layer was washed with brine (5 mL) and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to give the title reference compound (0.18 g) as a colorless solid (yield 49%).
Workup
- concentrationAfter the reaction mixture was concentrated under reduced pressure, water (5 mL)
- additionwas added
- extractionThe whole was extracted with ethyl acetate (10 mL)
- washthe organic layer was washed with brine (5 mL)
- dry with materialdried over anhydrous magnesium sulfate
- customAfter the solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-4766a5c982314071a60e0d1d8c197706
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193237B2
Reaction notes
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