1,4-Dioxane hydrochloride → 915386-24-2

HRID 732699Notes

Reaction equation

HRID 732699 reaction equation
C(OC([N:8]([CH2:21][C@@H:22]1[C@@H:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][N:24]([C:33]([O:35][C:36]2[CH:44]=[CH:43][C:39]([C:40]([OH:42])=[O:41])=[CH:38][CH:37]=2)=[O:34])[CH2:23]1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.[ClH:45].O1CCOCC1>>[ClH:45].[C:11]1([C@H:9]([NH:8][CH2:21][C@@H:22]2[C@@H:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][N:24]([C:33]([O:35][C:36]3[CH:37]=[CH:38][C:39]([C:40]([OH:42])=[O:41])=[CH:43][CH:44]=3)=[O:34])[CH2:23]2)[CH3:10])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68916166HCID 68916166, compound

Product 1

HCID 68913969915386-24-2

Procedure

A 1.05 g portion of 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}oxy)benzoic acid was dissolved in 10 ml of 4 M hydrogen chloride/1,4-dioxane solution and stirred at room temperature for 1Hour, and then the reaction solution was concentrated under a reduced pressure. In order to remove excess hydrogen chloride, the residue was dissolved in chloroform and again concentrated under a reduced pressure. By suspending the thus obtained residue in THF-toluene, 784 mg of 4-({[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}oxy)benzoic acid hydrochloride was obtained as a crude product. A 235 mg portion of the thus obtained crude product was suspended in THF-toluene and heated under reflux for 50 minutes, and then the resulting precipitate was collected by filtration to obtain 217 mg of 4-({[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}oxy)benzoic acid hydrochloride as a white solid.

Workup

  1. concentrationthe reaction solution was concentrated under a reduced pressure
  2. customIn order to remove excess hydrogen chloride
  3. dissolutionthe residue was dissolved in chloroform
  4. concentrationagain concentrated under a reduced pressure

Sources & evidence

ORD record
ord-2c3cf97453bf4941b504b624b97f67f8
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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