Ethyl Acetate → HCID 22168453, compound

HRID 390371

Reaction equation

HRID 390371 reaction equation
C[C:2]1(C)[N:7]([O])[C:6](C)(C)[CH2:5][CH:4](O)[CH2:3]1.C1(C(O)=O)CC1.[CH2:19]1[CH2:24][CH2:23][CH:22]([N:25]=[C:26]=[N:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:21][CH2:20]1.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.ClCCl.CCCCCC>[CH2:31]1[CH2:30][CH2:29][CH:28]([N:27]=[C:26]=[N:25][CH:22]2[CH2:23][CH2:24][CH2:19][CH2:20][CH2:21]2)[CH2:33][CH2:32]1.[CH3:22][N:25]([C:4]1[CH:3]=[CH:2][N:7]=[CH:6][CH:5]=1)[CH3:26]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 15655Cyclopropanecarboxylic acidHCID 137994Tempol

Product 1

HCID 22168453HCID 22168453, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent2×

Procedure

To a stirred solution of Tempol (1.72 g, 0.01 mmole), cyclopropanecarboxylic acid (0.946 g, 0.011 mmole), and DMAP (0.12, 0.001 mmole) in dichloromethane (25 ml) was added DCC (2.27 g, 0.11 mmole) and the mixture was stirred overnight at room temperature. The mixture was filtered over celite and the solution was evaporated under reduced pressure. The product was isolated by silica gel column chromatography using first hexane and then 10% ethyl acetate in hexane. Yield: 2.26 g (94.1). IR and NMR were consistent with the assigned structure.

Workup

  1. filtrationThe mixture was filtered over celite
  2. customthe solution was evaporated under reduced pressure
  3. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-63ec673a24ab40a1adfad9ee2f981012
Source dataset
uspto-grants-2013_02
Patent number
US08383648B2

Linked notes

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