Ethyl Acetate → 4'-(2-carboxy-2-methylpropyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-biphenylsulphonamide

HRID 1378360Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378360
C(=O)([O-])[O-].[Na+].[Na+].I[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([N:17]([C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])[C:18]1[C:23]([O:24][CH3:25])=[N:22][C:21]([CH3:26])=[CH:20][N:19]=1)(=[O:16])=[O:15].[C:34]([C:37]([CH3:49])([CH3:48])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1B(O)O)([OH:36])=[O:35].C(OCC)(=O)C>O.C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:34]([C:37]([CH3:49])([CH3:48])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:8]2[C:9]([S:14]([N:17]([C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])[C:18]3[C:23]([O:24][CH3:25])=[N:22][C:21]([CH3:26])=[CH:20][N:19]=3)(=[O:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:41][CH:40]=1)([OH:36])=[O:35]

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 18704832N-(isobutoxycarbonyl)-N-(3-methoxy-5-methyl-2-pyrazinyl)-2-iodobenzenesulphonamideHCID 21186352(2-Carboxy-2-methylpropyl)benzeneboronic acid

Produkt 1

HCID 229112884'-(2-carboxy-2-methylpropyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)-2-biphenylsulphonamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of sodium carbonate (2.86 g) in water (4 ml) was added to a soultion of 2-iodo- N-(isobutoxycarbonyl)- N-(3-methoxy-5-methylpyrazin-2-yl)benzenesulphonamide (6.2 g), (2-carboxy-2-methylpropyl)benzeneboronic acid (3.0 g) and tetrakis(triphenylphosphine)palladium(O) (235 mg) in toluene (30 ml) and ethanol (20 ml). The mixture was stirred vigorously and heated under reflux for 18 hours under an atmosphere of argon. Water (100 ml) and ethyl acetate (100 ml) were added and the organic layer was separated. The organic phase was extracted with saturated sodium bicarbonate solution (50 ml) and the aqueous phases were combined. The solution was acidifed with 6M hydrochloric acid and extracted with ethyl acetate (3×50 ml). The extracts were washed with water (50 ml) and saturated sodium chloride solution (50 ml) and then dried (MgSO4). Volatile material was removed by evaporation and the residue was triturated with etherexane (1:1 v/v) to give 4'-(2-carboxy-2-methylpropyl)- N-(isobutoxycarbonyl)- N-(3-methoxy-5 -methylpyrazin-2-yl)-2-biphenylsulphonamide (2.25 g); 1H NMR (d6 -DMSO): 0.6 (d, 6H), 1.1 (s, 6H), 1.5-1.7 (m, 1H), 2.52 (s, 3H), 2.85 (s, 2H), 3.8 (d, 2H), 3.95 (s, 3H), 7.15 (d, 2H), 7.25 (d, 2H), 7.3-7.4 (m, 1H), 7.7-7.8 (m, 2H), 8.15 (s, 1H), 8.5-8.6 (m, 1H), 12.3 (s, 1H).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 18 hours under an atmosphere of argon
  3. customthe organic layer was separated
  4. extractionThe organic phase was extracted with saturated sodium bicarbonate solution (50 ml)
  5. extractionextracted with ethyl acetate (3×50 ml)
  6. washThe extracts were washed with water (50 ml) and saturated sodium chloride solution (50 ml)
  7. dry with materialdried (MgSO4)
  8. customVolatile material was removed by evaporation
  9. customthe residue was triturated with etherexane (1:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-8cb2528eb8ff4ceb932cafccadbe0826
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668137

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