1,4-Dioxane hydrochloride → 3-methoxy-4-({[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)benzoic acid hydrochloride

HRID 732712Notes

Reaction equation

HRID 732712 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]([NH:35][C:36]2[CH:44]=[CH:43][C:39]([C:40]([OH:42])=[O:41])=[CH:38][C:37]=2[O:45][CH3:46])=[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:47].O1CCOCC1>O1CCOCC1>[ClH:47].[CH3:46][O:45][C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][C:36]=1[NH:35][C:33]([N:24]1[CH2:25][C@H:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:22]([CH2:21][NH:8][C@@H:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:23]1)=[O:34])[C:40]([OH:42])=[O:41]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 689103484-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)-3-methoxybenzoic acid

Product 1

HCID 689104233-methoxy-4-({[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)benzoic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

An 8.0 ml 1,4-dioxane solution of 226 mg of 4-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin 1-yl]carbonyl}amino)-3-methoxybenzoic acid was mixed with 2.0 ml of 4 M hydrogen chloride/1,4-dioxane at room temperature and stirred overnight at room temperature. The solvent was evaporated under a reduced pressure, and the residue was crystallized with 1,4-dioxane-diisopropyl ether to obtain 180 mg of 3-methoxy-4-({[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}amino)benzoic acid hydrochloride as a beige solid.

Workup

  1. customThe solvent was evaporated under a reduced pressure
  2. customthe residue was crystallized with 1,4-dioxane-diisopropyl ether

Sources & evidence

ORD record
ord-be69fa4d3a9140fe9ab6bdd789c38ab8
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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