1,4-Dioxane hydrochloride → Hydrochloric Acid

HRID 11839Notes

Reaction equation

HRID 11839 reaction equation
C([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([NH:26][C@@H:27]([CH2:31][CH2:32][CH2:33][NH:34][CH:35]2[C:44]3[N:43]=[CH:42][CH:41]=[CH:40][C:39]=3[CH2:38][CH2:37][CH2:36]2)[C:28]([OH:30])=[O:29])=[O:25])=[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:45].O1CCOCC1>CO>[ClH:45].[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([NH:26][C@@H:27]([CH2:31][CH2:32][CH2:33][NH:34][CH:35]2[C:44]3[N:43]=[CH:42][CH:41]=[CH:40][C:39]=3[CH2:38][CH2:37][CH2:36]2)[C:28]([OH:30])=[O:29])=[O:25])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21043734HCID 21043734, compound

Product 2

HCID 313Hydrochloric AcidHCID 69638672(2S)-2-((4-(N-2-picolylaminomethyl)phenylacetyl)amino)-5-(5,6,7,8-tetrahydroquinolin-8-yl)aminovaleric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 8-8 (18.0 mg) was dissolved in methanol (0.2 ml) and 4 mol/l hydrochloric acid/dioxane solution was added. The mixture was stirred for 1.5 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (1.0 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 (14.4 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 (1.0 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-67abb265325d4c0db000f071744365b3
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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