Hydrochloric Acid → HCID 18950599, compound

HRID 1492647Notes

Reaction equation

HRID 1492647 reaction equation
[C:1]([CH:5]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][N:15]2[C:19]3=[N:20][C:21]([CH3:25])=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]=[C:16]2[CH2:26][CH3:27])=[CH:9][C:8]=1[CH3:28])([O:3]C)=[O:2].[OH-].[Na+].Cl>CO>[C:1]([CH:5]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][N:15]2[C:19]3=[N:20][C:21]([CH3:25])=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]=[C:16]2[CH2:26][CH3:27])=[CH:9][C:8]=1[CH3:28])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53716375HCID 53716375, compound

Product 1

HCID 18950599HCID 18950599, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a magnetically stirred solution of 0.280 g (0.56 mmol) of the product of Step D in 4.0 mL methanol was added 0.5 mL of a 5.0N solution of sodium hydroxide and the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was adjusted to pH=6 with 1.0N hydrochloric acid and then concentrated in vacuo. The residue was then purified on a silica gel flash chromatography column eluted with CHCl3 --MeOH--NH4OH (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 0.238 g (87%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was then purified on a silica gel flash chromatography column
  3. washeluted with CHCl3 --MeOH--NH4OH (80:15:1)
  4. customEvaporation of the purified fractions
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-bb3a192722df45ca91116fe4785c2e8f
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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