1,4-Dioxane hydrochloride → HCID 68913863, compound

HRID 732698Notes

Reaction equation

HRID 732698 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][CH:42]=[CH:41][C:37]=2[C:38]([OH:40])=[O:39])=[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.Cl.O1CCOCC1>O1CCOCC1>[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:44]=[CH:43][CH:42]=[CH:41][C:37]=3[C:38]([OH:40])=[O:39])=[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 68912090HCID 68912090, compound

Product 1

HCID 68913863HCID 68913863, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 2.0 ml 1,4-dioxane solution of 145 mg of 2-({[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin 1-yl]carbonyl}oxy)benzoic acid was mixed with 1.0 ml of 4 M hydrogen chloride/1,4-dioxane at room temperature and stirred overnight at room temperature. The reaction solution was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 39 mg of 2-({[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}oxy)benzoic acid as a colorless amorphous substance.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6dd7bd1086224bf38c0b1ac9d4715ec8
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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