Ethyl Acetate → HCID 59864827, compound

HRID 2423277Notes

Reaction equation

HRID 2423277 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([OH:26])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:11]([N+:20]([O-:22])=[O:21])=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:19])=[CH:13]2.[C:27](OCC)(=O)[CH3:28]>C(O)C.S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:11]([N+:20]([O-:22])=[O:21])=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:19])=[CH:13]2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59864800HCID 59864800, compound

Product 1

HCID 59864827HCID 59864827, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.2 (1.65 g, 4.63 mmol) in ethanol (20 mL) with several drops of concentrated sulfuric acid was heated to reflux overnight. After 16 h, HPLC indicated that no 1.2 remained and the ethanol was removed in vacuo on a rotary evaporator. The concentrate was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The separated organic layer was washed with water then brine, stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a dark oil. The desired product was isolated by trituration of the residue with ethyl acetate to yield the desired product as an orange solid. The filtrate from trituration was chromatographed on silica gel, eluting with an ethyl acetate/hexane gradient, to afford additional product. LC-MS ESI (pos.) m/z: 385.0 (M+H).

Workup

  1. temperatureto reflux overnight
  2. customthe ethanol was removed in vacuo on a rotary evaporator
  3. customThe concentrate was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. washThe separated organic layer was washed with water
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  7. customto afford a dark oil

Sources & evidence

ORD record
ord-1a93138758e6474992c8fcf9b019daf5
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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