Sodium → Ibutilide

HRID 466367

反応式

HRID 466367 の反応式
[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]

参加物

8

反応物 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

生成物 1

HCID 60753Ibutilide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fb0211ba58e54922a4a3be53e4193a78
出典データセット
uspto-grants-1992_10
特許番号
US05155268

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