Water → HCID 15230547, compound

HRID 744093Notes

Reaction equation

HRID 744093 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[C:8](/[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)=[CH:9]\[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:33])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27]C(=O)C)=[C:21]([O:31][CH3:32])[CH:20]=2)[CH2:14][CH2:13]1)=[O:11].C(=O)([O-])[O-].[K+].[K+].O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[C:8](/[C:34]1[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=1)=[CH:9]\[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:33])[C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([OH:27])=[C:21]([O:31][CH3:32])[CH:20]=2)[CH2:14][CH2:13]1)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67731541HCID 67731541, compound

Product 1

HCID 15230547HCID 15230547, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of a compound of Example 91 (0.500 g) in methanol (20 ml) was added an aqueous solution saturated with potassium carbonate (10 ml), and the resulting mixture was stirred at room temperature for an hour. The reaction mixture was poured into water and extracted thrice with methylenechloride. The combined extract was washed with water, dried and concentrated. The residue was purified by liquid chromatography under medium pressure through two Lobar B columns. Fractions eluted with a 19:1 mixture of ethyl acetate and methanol were collected and worked up to afford the title compound (0.464 g) as a powder.

Workup

  1. extractionextracted thrice with methylenechloride
  2. extractionThe combined extract
  3. washwas washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by liquid chromatography under medium pressure through two Lobar B columns
  7. washFractions eluted with a 19:1 mixture of ethyl acetate and methanol
  8. customwere collected

Sources & evidence

ORD record
ord-eed5915c9a214e06956cfe5feaa14f67
Source dataset
uspto-grants-1996_09
Patent number
US05559109

Reaction notes

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