N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)-2-[alpha-hydroxy-4,5-(methylenedioxy)-2-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)benzyl]thieno[2,3-b]pyridine-3-sulfonamide → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-(2-hydroxyethyl)-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide

HRID 2393148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393148
[Cl:1][C:2]1[C:3]([CH3:47])=[N:4][O:5][C:6]=1[N:7]([CH2:41][O:42][CH2:43][CH2:44][O:45][CH3:46])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:20]([OH:40])[C:21]1[CH:26]=[C:25]2[O:27][CH2:28][O:29][C:24]2=[CH:23][C:22]=1[CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)(=[O:10])=[O:9]>C(O)(=O)C.O.C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[C:3]([CH3:47])=[N:4][O:5][C:6]=1[N:7]([CH2:41][O:42][CH2:43][CH2:44][O:45][CH3:46])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:20]([OH:40])[C:21]1[CH:26]=[C:25]2[O:27][CH2:28][O:29][C:24]2=[CH:23][C:22]=1[CH2:30][CH2:31][OH:32])(=[O:9])=[O:10]

Komponenten

6

Edukt 1

HCID 53873460N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)-2-[alpha-hydroxy-4,5-(methylenedioxy)-2-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)benzyl]thieno[2,3-b]pyridine-3-sulfonamide

Produkt 1

HCID 57235804N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-(2-hydroxyethyl)-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxy-methyl)-2-[α-hydroxy-4,5-(methylenedioxy)-2-(2-{[(1,1-dimethylethyl)dimethylsilyl]oxy}ethyl)benzyl]thieno[2,3-b]pyridine-3-sulfonamide (0.29 g, 0.40 mmoles) in acetic acid (3 ml), H2O (1 ml) and THF (1 ml) was stirred at ambient temperature for 18 hours, then diluted with EtOAc (100 ml) and washed with sat. NaHCO3 (2×200 ml). The organic layer was dried (MgSO4), filtered and concentrated to collect 0.23 g (94%) of the title compound as a yellow oil.

Aufarbeitung

  1. washwashed with sat. NaHCO3 (2×200 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto collect 0.23 g (94%) of the title compound as a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-8e88c0fd118a4b25951363a538ddce61
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05804585

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