Ethyl Acetate → Ot-551

HRID 2117390Notes

Reaction equation

HRID 2117390 reaction equation
[CH3:1][C:2]1([CH3:12])[N:7]([O])[C:6]([CH3:10])([CH3:9])[CH2:5][CH:4]([OH:11])[CH2:3]1.[CH:13]1([C:16](O)=[O:17])[CH2:15][CH2:14]1.C1CCC(N=C=NC2CCCCC2)CC1.C(OCC)(=[O:36])C>CN(C1C=CN=CC=1)C.ClCCl.CCCCCC>[OH:36][N:7]1[C:2]([CH3:12])([CH3:1])[CH2:3][CH:4]([O:11][C:16]([CH:13]2[CH2:15][CH2:14]2)=[O:17])[CH2:5][C:6]1([CH3:10])[CH3:9]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 15655Cyclopropanecarboxylic acidHCID 137994Tempol

Product 1

HCID 10131000Ot-551

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-01ff72d8c1854753af1b3e6b1aac4721
Source dataset
uspto-grants-2008_10
Patent number
US07442711B2

Reaction notes

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