Lansoprazole → HCID 20786423, Verbindung

HRID 2182843

Reaktionsgleichung

Reaktionsgleichung von HRID 2182843
[CH3:1][C:2]1[C:3]([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])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].[H-].[Na+].C1(C)C=CC(S(CCOC(=O)C)(=O)=O)=CC=1.[C:44]1([CH3:70])[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH2:54][O:55][C:56](=[O:69])[CH2:57][O:58][C:59]2[CH:64]=[CH:63][C:62]([S:65](Cl)(=[O:67])=[O:66])=[CH:61][CH:60]=2)(=[O:52])=[O:51])=[CH:46][CH:45]=1.C([O-])(O)=O.[Na+].ClS([O-])(=O)=O>C(Cl)Cl>[C:44]1([CH3:70])[CH:49]=[CH:48][C:47]([S:50]([CH2:53][CH2:54][O:55][C:56](=[O:69])[CH2:57][O:58][C:59]2[CH:64]=[CH:63][C:62]([S:65]([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:3]3[C:2]([CH3:1])=[C:7]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])[CH:6]=[CH:5][N:4]=3)=[O:16])(=[O:66])=[O:67])=[CH:61][CH:60]=2)(=[O:52])=[O:51])=[CH:46][CH:45]=1

Komponenten

8

Edukt 6

HCID 3883LansoprazoleHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate2×HCID 21989438SulfurochloridateHCID 58426230HCID 58426230, VerbindungHCID 59316688HCID 59316688, Verbindung

Produkt 1

HCID 20786423HCID 20786423, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a heterogeneous solution of 2-[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-ylmethanesulfinyl]-1H-benzimidazole (900 mg, 2.44 mmol) in 30 mL of CH2Cl2 was added 70 mg of NaH (2.92 mmol) at room temperature, during which time the mixture became homogeneous. To this clear reaction mixture was added the 4-chlorosulfonylphenoxy)acetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 4, 1.26 g, 2.92 mmol, 1.2 eq). About 1 g of solid NaHCO3 was added after the chlorosulfonate has dissolved completely in the reaction mixture. (Without addition of NaHCO3 the mixture became black when the reaction was complete.) Thereafter the solvent was removed by evaporation and the residual oil was purified by column chromatography (silica gel, CH2Cl2 to 4% MeOH in CH2Cl2) to give 1.75 g (94%) of the desired product (Intermediate 5) as an off-white foam.

Aufarbeitung

  1. dissolutionhas dissolved completely in the reaction mixture
  2. custom) Thereafter the solvent was removed by evaporation
  3. customthe residual oil was purified by column chromatography (silica gel, CH2Cl2 to 4% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-fedb963048944885a00ed1ff4b580582
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897227B2

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