Sodium → Ibutilide

HRID 466367

반응식

HRID 466367 반응식
[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]

참가 물질

8

반응물 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

생성물 1

HCID 60753Ibutilide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb0211ba58e54922a4a3be53e4193a78
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155268

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