Sodium Hydroxide → HCID 58232743, compound

HRID 1422430Notes

Reaction equation

HRID 1422430 reaction equation
C([O:3][C:4](=[O:40])[CH:5]([N:13]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]([O:30]CC)=[O:29])[CH2:23][CH2:22][N:21]([CH2:33][C:34]([O:36]CC)=[O:35])[CH2:20][C:19]2[N:39]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:14]1)[CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])C.[OH-].[Na+]>C(O)C.O>[C:28]([CH2:27][N:24]1[CH2:23][CH2:22][N:21]([CH2:33][C:34]([OH:36])=[O:35])[CH2:20][C:19]2[N:39]=[C:15]([CH:16]=[CH:17][CH:18]=2)[CH2:14][N:13]([CH:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[C:4]([OH:40])=[O:3])[CH2:26][CH2:25]1)([OH:30])=[O:29]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58232889HCID 58232889, compound

Product 1

HCID 58232743HCID 58232743, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

15 mg of the compound obtained in stage 2 (26.5 μmol) are dissolved in 40 μl of ethanol and 53 μl of 5N sodium hydroxide are added dropwise rapidly. The mixture is brought to reflux for 24 h. The reaction medium is diluted 10-fold with water and the pH is then adjusted to 6.5 by adding weakly acidic resin. The resin is filtered off and washed with water. A strongly basic resin is added to the filtrate and then filtered off and washed twice with water. The product is eluted with 50% acetic acid. After evaporation to dryness, the product is obtained in the form of brown crystals. m=8 mg. Yield=60%.

Workup

  1. temperatureto reflux for 24 h
  2. additionby adding weakly acidic resin
  3. filtrationThe resin is filtered off
  4. washwashed with water
  5. additionA strongly basic resin is added to the filtrate
  6. filtrationfiltered off
  7. washwashed twice with water
  8. washThe product is eluted with 50% acetic acid
  9. customAfter evaporation to dryness
  10. customthe product is obtained in the form of brown crystals

Sources & evidence

ORD record
ord-b2f4b768c6bc4bb3a1ad6bc1f58b744b
Source dataset
uspto-grants-2015_01
Patent number
US08926945B2

Reaction notes

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