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Triethylamine → 4-Isopropyl-N-[4-((1R,5S,6R)-3-propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamide

HRID 1173061
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1173061
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:14][C@@H:13]3[C@H:9]2[CH2:10][N:11]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:12]3)=[CH:4][CH:3]=1.[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20].C(N(CC)CC)C>O1CCCC1>[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C@@H:8]3[CH2:14][C@@H:13]4[C@H:9]3[CH2:10][N:11]([C:15](=[O:18])[CH2:16][CH3:17])[CH2:12]4)=[CH:6][CH:7]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 673664421-[(1R,5S,6R)-6-(4-aminophenyl)-3-aza-bicyclo[3.2.0]hept-3-yl]-propan-1-one

Produkt 1

HCID 673660504-Isopropyl-N-[4-((1R,5S,6R)-3-propionyl-3-aza-bicyclo[3.2.0]hept-6-yl)-phenyl]-benzenesulfonamideAusbeute 113,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

0.935 g of 1-((1R,5S,6R)-6-(4-amino-phenyl)-3-aza-bicyclo[3.2.0]hept-3-yl)-propan-1-one (3.83 mmol) were dissolved in 30 ml of tetrahydrofuran and 0.795 g of 4-isopropylbenzenesulfonyl chloride (3.64 mmol) and 1.6 ml of triethylamine (11.48 mmol) were added. After stirring for 18 h at room temperature, the solvent was evaporated under reduced pressure, the remaining material was partitioned between diethyl ether and water that was adjusted to alkaline pH with 1 N aqueous sodium hydroxide. The aqueous layer was reextracted three times with diethyl ether, and the combined organic layers were dried over magnesium sulfate, filtered, and the solvent was evaporated to yield 1.76 g of crude product that was used in the subsequent reaction step without further purification.

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. customthe remaining material was partitioned between diethyl ether and water that
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-092ca0ddbc774f70b49c60cf46acef0b
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07834048B2

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