Sodium → Ibutilide

HRID 466367

Reaction equation

HRID 466367 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:9]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:10](=O)[CH2:11][CH2:12][C:13](=[O:25])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=1)[CH3:8].CC1C=C(C(=O)C)C=CC=1NS(C)(=O)=O.[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>O1CCCC1.C(OCC)(=O)C>[CH2:7]([N:9]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10][CH2:11][CH2:12][CH:13]([C:14]1[CH:15]=[CH:16][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:18][CH:19]=1)[OH:25])[CH3:8]

Participants

8

Reactant 5

HCID 5360545SodiumHCID 6100505Dipotassium 2,3-dihydroxybutanedioateHCID 14891420N-Ethyl-n-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamideHCID 19873430N-(4-Acetyl-2-methylphenyl)methanesulfonamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 60753Ibutilide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of lithium aluminum hydride (0.86 g, 0.0227 mol) in dry tetrahydrofuran (30 ml) under nitrogen is cooled to 0° to -5° C. and treated dropwise during 25 minutes with a solution of N-ethyl-N-heptyl-γ-oxo-4-[(methylsulfonyl)amino]benzenebutanamide as prepared in Preparation 3 (3.0 g, 0.00757 mole) in THF (30 ml). After 2.5 hours this mixture is treated dropwise with a saturated solution of sodium, potassium tartrate (10 ml) and then with ethyl acetate. The mixture is filtered and the solid is extracted with ethyl acetate. The organic solutions are dried (MgSO4) and concentrated; the residual product is combined to give 2.10 g of N-[4-[4-(ethylheptylamino)-1-hydroxybutyl]phenyl]methanesulfonamide. By NMR this material is the same as an authentic sample obtained from another reaction and purified by silica gel chromatography with 0.5% NH4OH-6% MeOH--CH2Cl2.

Workup

  1. temperatureis cooled to 0° to -5° C.
  2. filtrationThe mixture is filtered
  3. extractionthe solid is extracted with ethyl acetate
  4. dry with materialThe organic solutions are dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb0211ba58e54922a4a3be53e4193a78
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Linked notes

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