1,4-Dioxane hydrochloride → HCID 86628553, compound

HRID 732688Notes

Reaction equation

HRID 732688 reaction equation
C(C([N:7]([CH2:20][C@@H:21]1[C@@H:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:24][N:23]([C:32]([C:34]2[CH:46]=[CH:45][C:37]([O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:36][CH:35]=2)=[O:33])[CH2:22]1)[C@@H:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:9])=O)(C)(C)C.Cl.O1CCOCC1>O1CCOCC1>[C:10]1([C@H:8]([NH:7][CH2:20][C@@H:21]2[C@@H:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:24][N:23]([C:32]([C:34]3[CH:35]=[CH:36][C:37]([O:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:45][CH:46]=3)=[O:33])[CH2:22]2)[CH3:9])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86628554HCID 86628554, compound

Product 1

HCID 86628553HCID 86628553, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixed solution of 264 mg of ethyl (4-{[(3R,4S)-3-({(tert-butylcarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}phenoxy)acetate and 3.0 ml of 1,4-dioxane was mixed with 1.0 ml of 4 M hydrogen chloride/1,4-dioxane and stirred at room temperature for 24Hours. The reaction solution was concentrated under a reduced pressure, and the residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 174 mg of ethyl (4-{[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}phenoxy)acetate as a colorless amorphous substance. FP: 537.

Workup

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

Sources & evidence

ORD record
ord-3fdbd75ca46a46278c13bffd8c698001
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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