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1-Naphthalenecarbonyl chloride → N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(methyloxy)phenyl)methyl)ethyl)-1-naphthalenecarboxamide

HRID 1610293
Notes
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Reaction equation

HRID 1610293 reaction equation
[NH2:1][CH:2]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)[OH:4].[C:21]1([C:31](Cl)=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[F:11][C:8]1[CH:7]=[CH:6][C:5]([CH:3]([OH:4])[CH:2]([NH:1][C:31]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][CH:22]=2)=[O:32])[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[CH:10][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 22261918(1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-(4-(methyloxy)phenyl)-1-propanol

Product 1

HCID 22261663N-((1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((4-(methyloxy)phenyl)methyl)ethyl)-1-naphthalenecarboxamideYield 89%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-(4-(methyloxy)phenyl)-1-propanol (450 mg, 1.64 mmol) in ethyl acetate (15 ml) were added 1-naphthoyl chloride (369 ml, 2.45 mmol) and saturated aqueous sodium hydrogen carbonate (15 ml) and the mixture was stirred overnight at room temperature. The reaction solution was diluted with water (100 ml) and extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (622 mg, 89%).

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0a2d0bc3b8024ce697a95559b557aadd
Source dataset
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06982348B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes