1,4-Dioxane hydrochloride → Hydrochloric Acid

HRID 11844Notes

Reaction equation

HRID 11844 reaction equation
C([N:8]([CH2:16][C:17]1[O:21][C:20]([C:22]([NH:24][C@@H:25]([CH2:29][CH2:30][CH2:31][NH:32][CH:33]2[C:42]3[N:41]=[CH:40][CH:39]=[CH:38][C:37]=3[CH2:36][CH2:35][CH2:34]2)[C:26]([OH:28])=[O:27])=[O:23])=[CH:19][CH:18]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)(OC(C)(C)C)=O.[ClH:43].O1CCOCC1>CO>[ClH:43].[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][CH2:16][C:17]1[O:21][C:20]([C:22]([NH:24][C@@H:25]([CH2:29][CH2:30][CH2:31][NH:32][CH:33]2[C:42]3[N:41]=[CH:40][CH:39]=[CH:38][C:37]=3[CH2:36][CH2:35][CH2:34]2)[C:26]([OH:28])=[O:27])=[O:23])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21043738HCID 21043738, compound

Product 2

HCID 313Hydrochloric AcidHCID 69638153HCID 69638153, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 11-5 (30.6 mg) was dissolved in methanol (0.7 ml), and 4 mol/l hydrochloric acid/dioxane solution (0.7 ml) was added. The mixture was stirred for 3 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (1 g, chloroform/methanol/water=7/3/0.5). The obtained product was added with an aqueous solution of hydrochloric acid, concentrated and then azeotropically distilled with water. The resulting solid was washed with ether to obtain a hydrochloride of the title compound (22.7 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed by distillation
  3. customThe residue was purified by silica gel column chromatography (1 g, chloroform/methanol/water=7/3/0.5)
  4. additionThe obtained product was added with an aqueous solution of hydrochloric acid
  5. concentrationconcentrated
  6. distillationazeotropically distilled with water
  7. washThe resulting solid was washed with ether

Sources & evidence

ORD record
ord-f9b2fbe11f024165adc3b05c701f2695
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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