Acetic Acid → HCID 54234952, compound

HRID 482463Notes

Reaction equation

HRID 482463 reaction equation
[CH:1]1(N=C=NC2CCCCC2)CCCC[CH2:2]1.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH:27]=[C:26]([CH3:29])[CH2:25][C@H:24]1[C:30]([OH:32])=[O:31])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O)C.C(O)(=O)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:31][C:30]([C@@H:24]1[CH2:25][C:26]([CH3:29])=[CH:27][CH2:28][N:23]1[C:21]([O:20][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:22])=[O:32])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 22885597HCID 22885597, compound

Product 1

HCID 54234952HCID 54234952, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1,3-Dicyclohexylcarbodiimide (4.3 g, 20.8 mmol) was added to a stirred solution of the product from (f) above (3.35 g, 13.9 mmol), ethanol (4.1 ml, 69.4 mmol) and 4-dimethylaminopyridine (1.7 g, 13.9 mmol) in dichloromethane (40 ml). After 18 hours at room temperature, glacial acetic acid (0.4 ml) was added and the reaction mixture stirred for a further 0.5 hour before being filtered. The residue obtained by evaporation of the filtrate under reduced pressure was partitioned between ether and water, then the organic phase washed successively with 1M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine, dried (MgSO4) and evaporated under reduced pressure to give an oil (5.15 g), which was purified by chromatography on silica gel, using hexane:ether (4:1) as eluant, to furnish the required product (3.4 g) as a clear oil. Rf 0.30 (SS 4). m/e 270 (M+H)+.

Workup

  1. filtrationbefore being filtered
  2. customThe residue obtained by evaporation of the filtrate under reduced pressure
  3. customwas partitioned between ether and water
  4. washthe organic phase washed successively with 1M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6587d896b2484d22b704c4c621c826bf
Source dataset
uspto-grants-1998_08
Patent number
US05798352

Reaction notes

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