Aniline → Ethyl 1-(phenylaminocarbonyl)cyclopropanecarboxylate
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]([OH:11])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[C:37]1([NH:36][C:9]([C:6]2([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]2)=[O:11])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-(ethoxycarbonyl)cyclopropane carboxylic acid (7.4 g, 46.84 mmol) in dry CH2Cl2 (70 mL) was added HATU (35.62 g, 93.67 mmol) at 0° C. After stirring for 10 minutes, a solution of the aniline (8.71 g, 93.67 mmol) and Et3N-(9.48 g, 93.67 mmol) in dry CH2Cl2 (30 mL) was then added and the reaction mixture was continued to stir at 40° C. for 24 hrs. The reaction mixture was quenched with water (30 mL) and extracted with CH2Cl2 (100 mL×3). The combined organic phases were dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was chromatographed with a silica gel column (1:5 (v/v) EtOAc/n-hexane) to afford the title compound as a pale yellow solid (9.7 g, 89%).
Workup
- stirringto stir at 40° C. for 24 hrs
- customThe reaction mixture was quenched with water (30 mL)
- extractionextracted with CH2Cl2 (100 mL×3)
- dry with materialThe combined organic phases were dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was chromatographed with a silica gel column (1:5 (v/v) EtOAc/n-hexane)
Sources & evidence
- ORD record
- ord-fb3f94047cfc4fa9913ebcbb365a26cd
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293897B2
Reaction notes
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