1,4-Dioxane hydrochloride → Hydrochloric Acid

HRID 11868Notes

Reaction equation

HRID 11868 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]([CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]([NH:29][C@@H:30]([CH2:34][CH2:35][CH2:36][NH:37][C@H:38]2[C:47]3[N:46]=[CH:45][CH:44]=[CH:43][C:42]=3[CH2:41][CH2:40][CH2:39]2)[C:31]([OH:33])=[O:32])=[O:28])=[CH:19][CH:18]=1)C(OC(C)(C)C)=O.[ClH:48].O1CCOCC1>CO>[ClH:48].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][CH2:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27]([NH:29][C@@H:30]([CH2:34][CH2:35][CH2:36][NH:37][C@H:38]2[C:47]3[N:46]=[CH:45][CH:44]=[CH:43][C:42]=3[CH2:41][CH2:40][CH2:39]2)[C:31]([OH:33])=[O:32])=[O:28])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21043731(2S)-2-(4-(N-2-picolyl-N-Boc aminomethyl)naphthoylamino)-5-((8R)-5,6,7,8-tetrahydroquinolin-8-ylamino)valeric Acid

Product 2

HCID 313Hydrochloric AcidHCID 21043730(2S)-2-(4-(N-2-picolylaminomethyl)naphthoylamino)-5-((8R)-5,6,7,8-tetrahydroquinolin-8-ylamino)valeric Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in Example 54-3 (7.2 mg) was dissolved in methanol (0.15 ml) and 4 mol/l hydrochloric acid/dioxane solution (0.15 ml) was added. After 2 hours, the reaction solution was concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol/water=7/3/0.5). After the addition of 1 mol/l hydrochloric acid, the residue was concentrated and subjected to azeotropic distillation with methanol to obtain hydrochloride of the title compound (6.3 mg) as a white solid.

Workup

  1. concentrationthe reaction solution was concentrated
  2. customThe residue was purified by silica gel column chromatography (chloroform/methanol/water=7/3/0.5)
  3. additionAfter the addition of 1 mol/l hydrochloric acid
  4. concentrationthe residue was concentrated
  5. distillationsubjected to azeotropic distillation with methanol

Sources & evidence

ORD record
ord-7d03949ae1e54900937fdaebc8008d05
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

Loading…