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.CCN(CC)CC>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
6
Reactant 4
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-f96bb16697e94af587a9c9bcb8ef1bd5
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426585B2
Reaction notes
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