Water → HCID 178523111, compound

HRID 1767570Notes

Reaction equation

HRID 1767570 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C[O:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:13]3=[C:12]([CH2:24][CH2:25][NH:26][C:27]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[O:28])[C:11]=2[N:34]=1.O.C(=O)([O-])O.[Na+]>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[N:14]3[CH2:15][CH2:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:13]3=[C:12]([CH2:24][CH2:25][NH:26][C:27]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[O:28])[C:11]=2[N:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 18758231HCID 18758231, compound

Product 1

HCID 178523111HCID 178523111, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an inert atmosphere, 582 mg (4.36 mmol) of aluminium chloride are added to a solution of 350 mg (0.87 mmol) of the compound of Example 11 in 15 ml of dichloromethane. The reaction mixture is refluxed for 6 hours before being hydrolysed with water. The aqueous phase is neutralised with a sodium hydrogen carbonate solution and extracted with dichloromethane. After drying over magnesium sulphate and removal of the solvents by evaporation, the residue is purified by flash chromatography over silica gel (eluant:ethyl acetate/methanol, 95:5) and then by washing with a hexane/diethyl ether mixture to yield the title compound in the form of a white solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. extractionextracted with dichloromethane
  3. dry with materialAfter drying over magnesium sulphate and removal of the solvents by evaporation
  4. customthe residue is purified by flash chromatography over silica gel (eluant:ethyl acetate/methanol, 95:5)
  5. washby washing with a hexane/diethyl ether mixture

Sources & evidence

ORD record
ord-21e6d7886eaf45fea55aedebc2d94ba8
Source dataset
uspto-grants-2007_06
Patent number
US07235550B2

Reaction notes

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