1,4-Dioxane hydrochloride → Hydrochloric Acid

HRID 11843Notes

Reaction equation

HRID 11843 reaction equation
C([N:8]([CH2:16][CH2:17][C:18]1[CH:41]=[CH:40][C:21]([C:22]([NH:24][C@@H:25]([CH2:29][CH2:30][CH2:31][NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[C:26]([OH:28])=[O:27])=[O:23])=[CH:20][CH:19]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)(OC(C)(C)C)=O.[ClH:42].O1CCOCC1>CO>[ClH:42].[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:24][C@@H:25]([CH2:29][CH2:30][CH2:31][NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[C:26]([OH:28])=[O:27])=[O:23])=[CH:40][CH:41]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21043763(S)-2-(4-(N-Boc-2-picolylaminoethyl)benzoyl)amino-5-(2-picolylamino)valeric Acid

Product 2

HCID 313Hydrochloric AcidHCID 69638373HCID 69638373, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 10-1 (13.9 mg) was dissolved in methanol (0.28 ml) and 4 mol/l hydrochloric acid/dioxane solution (0.28 ml) was added to the solution. The mixture was stirred for 75 minutes at room temperature. After the completion of the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (0.5 g, chloroform/methanol/water=7/3/0.5). The obtained product was added with 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 (13.8 mg) as a white solid.

Workup

  1. customAfter the completion of the reaction
  2. customthe solvent was removed by distillation
  3. customThe residue was purified by silica gel column chromatography (0.5 g, chloroform/methanol/water=7/3/0.5)
  4. additionThe obtained product was added with 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-f60a1a72dfff4c97885528a0b47a17df
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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