2-Aminophenol → Methyl 1-((2-hydroxyphenyl)carbamoyl)cyclopropanecarboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]([O-:10])=O)[CH2:7][CH2:6]1)=[O:4].[K+].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[OH:34]>C1COCC1.C(OCC)(=O)C.CN(C=O)C>[OH:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[NH:27][C:8]([C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]1)=[O:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a stirred suspension of potassium 1-(methoxycarbonyl)cyclopropanecarboxylate (182 mg, 1 mmol) in 3 mL THF at room temperature under nitrogen was added 15 μL of DMF. Oxalyl chloride (87 μL, 1 mmol) was then added neat dropwise by syringe. After stirring at ambient temperature for 2 hours, the reaction was cooled to 0° C. and treated with DIEA (0.497 ml, 2.85 mmol) followed by 2-aminophenol (104 mg, 0.951 mmol) neat as a solid. The cooling bath was allowed to melt and the reaction was then stirred at ambient temperature overnight. The reaction was diluted to 30 mL with ethyl acetate and washed with 2N HCl, water, saturated sodium bicarbonate and brine. The organics were dried (MgSO4), filtered and concentrated to a yellow solid (147 mg, 68% yield).
Workup
- temperaturethe reaction was cooled to 0° C.
- stirringthe reaction was then stirred at ambient temperature overnight
- washwashed with 2N HCl, water, saturated sodium bicarbonate and brine
- dry with materialThe organics were dried (MgSO4)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-0dab543180ec49db89f37c8404b3c26c
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723330B2
Reaction notes
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