Triethylamine → (S)-N-(1-Hydroxybutan-2-yl)-2-nitrobenzenesulfonamide

HRID 253005Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253005
C(N(CC)CC)C.[NH2:8][C@@H:9]([CH2:12][CH3:13])[CH2:10][OH:11].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23](Cl)(=[O:25])=[O:24])([O-:16])=[O:15].C(=O)([O-])O.[Na+]>O1CCCC1>[OH:11][CH2:10][C@@H:9]([NH:8][S:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N+:14]([O-:16])=[O:15])(=[O:24])=[O:25])[CH2:12][CH3:13]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 1200842-Amino-1-butanol, (+)-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 66861496(S)-N-(1-Hydroxybutan-2-yl)-2-nitrobenzenesulfonamideAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triethylamine (0.94 ml, 6.74 mmol) was added to a solution of 400 mg (4.49 mmol) of (S)-2-aminobutan-1-ol in tetrahydrofuran (5 ml), and the mixture was stirred at room temperature for 10 min. 2-Nitrobenzenesulfonyl chloride (995.1 mg, 4.49 mmol) was added to the solution, and the mixture was stirred at room temperature for 15 min. A saturated aqueous sodium hydrogencarbonate solution was added thereto to stop the reaction, and the reaction solution was then extracted with ethyl acetate, was dried over anhydrous sodium sulfate, and was filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 1.22 g (yield 99%) of the title compound.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. customthe reaction
  3. extractionthe reaction solution was then extracted with ethyl acetate
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-561b8a09e87945bf98599213f9276bfa
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07871982B2

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