Benzenesulfonyl chloride → HCID 67607322, Verbindung

HRID 1619543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619543
[NH2:1][CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5][C@@H:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1)=[O:4].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[C:14]1([CH:2]([NH:1][S:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:28])=[O:27])[C:3]([O:5][C@@H:6]2[CH:11]3[CH2:10][CH2:9][N:8]([CH2:13][CH2:12]3)[CH2:7]2)=[O:4])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 59401091(R)-quinuclidin-3-yl 2-amino-2-phenylacetate

Produkt 1

HCID 67607322HCID 67607322, VerbindungAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(R)-quinuclidin-3-yl 2-amino-2-phenylacetate (I30) (100 mg, 0.38 mmol) was dissolved in DCM (4 ml) and TEA (0.11 ml, 0.77 mmol). Benzenesulfonyl chloride (59 μl, 0.46 mmol) was added and the solution was stirred at RT for 1 hour. The volatiles were evaporated and the residue was purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.3) to obtain (R)-quinuclidin-3-yl 2-phenyl-2-(phenylsulfonamido)acetate (101 mg; 66% yield).

Aufarbeitung

  1. customThe volatiles were evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.3)

Quellen und Nachweise

ORD-Eintrag
ord-11d3885830da43638536fe3a7d8fb8f9
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772314B2

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