Diglycolamine → Methyl 3-((2-(2-hydroxyethoxy)ethyl)carbamoyl)benzoate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:47][CH2:48][CH2:49][O:50][CH2:51][CH2:52][OH:53]>CN(C)C=O>[OH:53][CH2:52][CH2:51][O:50][CH2:49][CH2:48][NH:47][C:8]([C:7]1[CH:6]=[C:5]([CH:13]=[CH:12][CH:11]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Into a 1000-mL round bottom flask, was placed a solution of 3-(methoxycarbonyl)benzoic acid (20 g, 111.11 mmol, 1.00 equiv) in N,N-dimethylformamide (500 mL), HATU (63.2 g, 166.32 mmol, 1.50 equiv), N,N-diisopropylethylamine (21.5 g, 166.67 mmol, 1.50 equiv), 2-(2-aminoethoxy)ethanol (23.3 g, 221.90 mmol, 2.00 equiv). The resulting solution was stirred for overnight at 25° C. The resulting mixture was concentrated under vacuum. The resulting solution was dissolved in 200 mL of ethyl acetate. The resulting mixture was washed with 10×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane:methanol (100:1). This resulted in 15 g (51%) of methyl 3-((2-(2-hydroxyethoxy)ethyl)carbamoyl)benzoate as red oil.
Workup
- customInto a 1000-mL round bottom flask, was placed
- concentrationThe resulting mixture was concentrated under vacuum
- dissolutionThe resulting solution was dissolved in 200 mL of ethyl acetate
- washThe resulting mixture was washed with 10×200 mL of brine
- dry with materialThe mixture was dried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThis resulted in 15 g (51%) of methyl 3-((2-(2-hydroxyethoxy)ethyl)carbamoyl)benzoate as red oil
Sources & evidence
- ORD record
- ord-2e389921e02b4662a4ee18af8e8208a0
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301951B2
Reaction notes
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