Hydrogen chloride-ethyl acetate → (S)-4-[2-Hydroxy-3-([4-(4-carbamoylphenoxy)phenyl]-2-methylpropylamino)propoxy]carbazole Hydrochloride

HRID 2119838Notes

Reaction equation

HRID 2119838 reaction equation
[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37](=[O:39])[NH2:38])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.[ClH:40].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:40].[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:25]=[CH:26][C:27]([O:30][C:31]2[CH:36]=[CH:35][C:34]([C:37](=[O:39])[NH2:38])=[CH:33][CH:32]=2)=[CH:28][CH:29]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 53754997(S)-4-[2-Hydroxy-3-([4-(4-carbamoylphenoxy)phenyl]-2-methylpropylamino)propoxy]carbazole

Product 1

HCID 69584407(S)-4-[2-Hydroxy-3-([4-(4-carbamoylphenoxy)phenyl]-2-methylpropylamino)propoxy]carbazole Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of the product from example 85 (11.01 g, 21.03 mmol) in 180 mL ethyl acetate (180 mL) was treated with a 1N HCl/ethyl acetate (21 mL) solution at ambient temperature. The resulting slurry was stirred for approximately 1 hour at room temperature. The slurry was pressure filtered under nitrogen through a stainless steel filter. The filter cake was washed three times with ethyl acetate (30 mL) and dried under a nitrogen purge for 2 hours. The filter cake was then dried in a vacuum oven at 60° C. overnight. This afforded 10.46 g (88.8%) of product as a white solid. EA: Calculate for C32H34ClN3O4: C 68.63, H 6.12, N 7.50. Found: C 68.58, H 5.89, N 7.17.

Workup

  1. filtrationfiltered under nitrogen through a stainless steel
  2. filtrationfilter
  3. washThe filter cake was washed three times with ethyl acetate (30 mL)
  4. customdried under a nitrogen
  5. custompurge for 2 hours
  6. customThe filter cake was then dried in a vacuum oven at 60° C. overnight

Sources & evidence

ORD record
ord-a0d6057f187544fd94708313a825dd65
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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