Sulfuryl chloride → HCID 20786440, Verbindung

HRID 2182872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2182872
[Na].[CH3:2][O:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[O:16])[C:9]=1[CH3:26].C([O-])(O)=O.[Na+].S(Cl)(Cl)(=O)=O.[C:37]1([CH3:61])[CH:42]=[CH:41][C:40]([S:43]([CH2:46][CH2:47][O:48][C:49](=[O:60])[C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([S:56](Cl)(=[O:58])=[O:57])[CH:51]=2)(=[O:45])=[O:44])=[CH:39][CH:38]=1>C(Cl)Cl.O.CCN(CC)CC>[C:37]1([CH3:61])[CH:42]=[CH:41][C:40]([S:43]([CH2:46][CH2:47][O:48][C:49](=[O:60])[C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([S:56]([N:21]3[C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[N:18]=[C:17]3[S:15]([CH2:14][C:10]3[C:9]([CH3:26])=[C:8]([O:7][CH2:6][CH2:5][CH2:4][O:3][CH3:2])[CH:13]=[CH:12][N:11]=3)=[O:16])(=[O:58])=[O:57])[CH:51]=2)(=[O:45])=[O:44])=[CH:39][CH:38]=1

Komponenten

8

Edukt 4

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 9821387(S)-Rabeprazole sodiumHCID 224793682-(4-Methylbenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

Produkt 1

HCID 20786440HCID 20786440, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-1H-benzimidazole sodium salt (RABEPRAZOLE sodium salt, 1.0 g, 2.62 mmol), 5 mL of Et3N, and about 1 g of NaHCO3 in CH2Cl2 (15 mL) was added the sulfonyl chloride (Intermediate 43, 1.27 g, 3.15 mmol, 1.2 eq) in CH2Cl2 at room temperature, and then the mixture was stirred for 1.5 h. Thereafter water was added, the mixture was extracted with CH2Cl2, and the organic layers were dried, and concentrated. The resulting residual oil was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to yield 1.5 g (76%) of 3-{2-[4-(3-methoxy-propoxy)-3-methyl-pyridin-2-yl-methanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 48) as an off-white foam.

Aufarbeitung

  1. extractionthe mixture was extracted with CH2Cl2
  2. customthe organic layers were dried
  3. concentrationconcentrated
  4. customThe resulting residual oil was purified by column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3b232747fad24538811f8e8e3aea7101
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897227B2

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