Water → HCID 73207857, compound

HRID 2179913Notes

Reaction equation

HRID 2179913 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OC1[CH:23]([N:24]2[CH2:29][CH2:28][CH:27]([CH3:30])[CH2:26][CH2:25]2)[C:22]2=[CH:31][CH:19]([O:20][C:21]2=[O:32])[CH:18]2[CH:14]([O:15][C:16](=[O:34])[CH:17]2[CH3:33])[CH2:13][C:12]2(C)[CH:10]1[O:11]2.O>N1C=CC=CC=1>[C:5]([O:4][CH:1]1[CH:23]([N:24]2[CH2:25][CH2:26][CH:27]([CH3:30])[CH2:28][CH2:29]2)[C:22]2=[CH:31][CH:19]([O:20][C:21]2=[O:32])[CH:18]2[CH:14]([O:15][C:16](=[O:34])[CH:17]2[CH3:33])[CH2:13][C:12]2([CH3:10])[CH:2]1[O:11]2)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 73207834HCID 73207834, compound

Product 1

HCID 73207857HCID 73207857, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (150 μmol; 15 μl) is added to a solution of the compound of Example 9 (100 μmol; 40 mg) in pyridine (0.5 ml). The solution obtained is stirred for 20 hours then the reaction mass is poured into water. The aqueous phase is extracted twice with ethyl acetate and the organic phase obtained is washed with water then with a solution of sodium chloride. The organic phase is dried over magnesium sulphate, filtered then evaporated. The residue is eluted on silica with a mixture of isopropyl acetate and dichloromethane (20/80). 16 mg of product is obtained in the form of a white powder.

Workup

  1. customThe solution obtained
  2. extractionThe aqueous phase is extracted twice with ethyl acetate
  3. customthe organic phase obtained
  4. washis washed with water
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. customthen evaporated
  8. washThe residue is eluted on silica with a mixture of isopropyl acetate and dichloromethane (20/80)

Sources & evidence

ORD record
ord-5bea74169f544f008b31b1b06693c7bd
Source dataset
uspto-grants-2005_05
Patent number
US06887869B2

Reaction notes

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