Hydrochloric Acid → HCID 15289391, compound

HRID 257822Notes

Reaction equation

HRID 257822 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([C:30]([O:32]C)=[O:31])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:18]([CH2:34][CH2:35][CH3:36])[CH:17]=2)[C:13](=[O:37])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:38])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO.O>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:23]([C:30]([OH:32])=[O:31])[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[C:18]([CH2:34][CH2:35][CH3:36])[CH:17]=2)[C:13](=[O:37])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:38])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20081758HCID 20081758, compound

Product 1

HCID 15289391HCID 15289391, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Procedure

To a solution the product of Example 3, Step A (11 mg; 0.22 mmol) in MeOH (2 mL) was added NaOH (1.5 eq, 2.0N) and a few drops of water. After stirring for 20 hours at room temperature, the reaction mixture was concentrated in vacuo, dissolved in water/THF, treated with HCl (5 eq) for 30 minutes at room temperature, concentrated in vacuo, and chromatographed on a Sephadex LH-20 column eluting with MeOH to afford 11 mg (99%) of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water/THF
  3. concentrationconcentrated in vacuo
  4. customchromatographed on a Sephadex
  5. washcolumn eluting with MeOH

Sources & evidence

ORD record
ord-6d137329a298434f99b892d04ee0e350
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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