1,4-Dioxane hydrochloride → HCID 68912444, compound

HRID 732691Notes

Reaction equation

HRID 732691 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]([S:33]([C:36]2[CH:44]=[CH:43][C:39]([C:40]([OH:42])=[O:41])=[CH:38][CH:37]=2)(=[O:35])=[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>C(OCC)C>[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]([S:33]([C:36]3[CH:44]=[CH:43][C:39]([C:40]([OH:42])=[O:41])=[CH:38][CH:37]=3)(=[O:35])=[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

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68915476HCID 68915476, compound

Product 1

HCID 68912444HCID 68912444, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 320 mg portion of 4-{[(3S,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]sulfonyl}benzoic acid was dissolved at room temperature in 3.0 ml of 4 M hydrogen chloride/1,4-dioxane solution and stirred for 24Hours. The reaction solution was diluted with diethyl ether and then concentrated under a reduced pressure, the thus obtained residue was dissolved in THF and mixed with diisopropyl ether, and the thus precipitated solid was collected by filtration and dried under a reduced pressure to obtain 183 mg of 4-{[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]sulfonyl}benzoic acid hydrochloride as a colorless solid.

Workup

  1. concentrationconcentrated under a reduced pressure
  2. dissolutionthe thus obtained residue was dissolved in THF
  3. additionmixed with diisopropyl ether
  4. filtrationthe thus precipitated solid was collected by filtration
  5. customdried under a reduced pressure

Sources & evidence

ORD record
ord-2005f3c305534961ac99d2b46ac432d9
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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