Water → HCID 131720620, compound

HRID 1599378Notes

Reaction equation

HRID 1599378 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][NH:6][C:7]([O:9][C@@H:10]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1)[C@@H:11]1[N:16]2[CH2:17][CH2:18][C@H:13]([C@@H:14]([CH:19]=[CH2:20])[CH2:15]2)[CH2:12]1)=[O:8])C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25]([N:24]=[CH:23][CH:22]=[C:21]2[C@H:10]([O:9][C:7]([NH:6][CH2:5][C:4]([OH:33])=[O:3])=[O:8])[C@@H:11]2[N:16]3[CH2:17][CH2:18][C@H:13]([C@@H:14]([CH:19]=[CH2:20])[CH2:15]3)[CH2:12]2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 131720619HCID 131720619, compound

Product 1

HCID 131720620HCID 131720620, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 120 mg (0.26 mmol) of (8) in 2 ml of methanol was added 200 mg of potassium carbonate and 0.5 ml of water. The mixture was heated to reflux for 2 h and cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated to remove methanol. The residue was redissolved in 2 ml of water and 1N HCl was added dropwise to the solution until the pH reached 7. The aqueous solution was concentrated, 100 ml of methanol was added and filtered. The filtrate was concentrated and yielded 95 mg (0.22 mmol, 85%) of (9).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customto remove methanol
  6. dissolutionThe residue was redissolved in 2 ml of water
  7. addition1N HCl was added dropwise to the solution until the pH
  8. concentrationThe aqueous solution was concentrated
  9. addition100 ml of methanol was added
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1f3ed85a3782422ea496879916817719
Source dataset
uspto-grants-1998_04
Patent number
US05741715

Reaction notes

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