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Hydrochloric Acid → N-[3-[1-(3,3-dimethylbutyl)-4-hydroxy-2-oxo-4a,5,6,7,8,8a-hexahydroquinolin-3-yl]-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide

HRID 731295
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 731295
C(O[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[N:12]([CH2:33][CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:13](=[O:32])[CH2:14][C:15]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:18]=2[S:17](=[O:31])(=[O:30])[N:16]=1)=[O:5])C.[O-]CC.[Na+].Cl>C(O)C.C(OCC)(=O)C>[CH3:37][C:35]([CH3:38])([CH3:36])[CH2:34][CH2:33][N:12]1[C:13](=[O:32])[C:14]([C:15]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][C:18]=3[S:17](=[O:31])(=[O:30])[N:16]=2)=[C:4]([OH:5])[CH:6]2[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 69065399cis-2-{(3,3-Dimethylbutyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}-cyclohexanecarboxylic acid ethyl ester

Produkt 1

HCID 135955949N-[3-[1-(3,3-dimethylbutyl)-4-hydroxy-2-oxo-4a,5,6,7,8,8a-hexahydroquinolin-3-yl]-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of cis-2-{(3,3-dimethylbutyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}-cyclohexanecarboxylic acid ethyl ester (138.7 mg, 0.243 mmol) in absolute ethanol (10 mL) was added a 21% w/w solution of sodium ethoxide in ethanol (0.91 mL, 2.44 mmol). After stirring at 60° C. for 13 h, the mixture was diluted with ethyl acetate and acidified with 1.0 M aqueous hydrochloric acid solution to pH 1. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude mixture was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-100% ethyl acetate in hexanes) to afford the desired product, N-{3-[2-(3,3-dimethylbutyl)-5-hydroxy-3-oxo-2-aza-bicyclo[4.4.0]dec-4-en-4-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (44.3 mg, 0.084 mmol, 35%), as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 0.94 (9H, s), 1.10-1.87 (9H, m), 2.32 (1H, bs), 3.04 (3H, s), 2.92-3.82 (4H, m), 7.47-7.58 (3H, m), 10.13 (1H, bs). LC-MS (ESI) calcd for C23H32N4O6S2 524.18, found 525.3 [M+H+]. Anal. calcd for C23H32N4O6S2: C, 52.65; H, 6.15; N, 10.68; S, 12.22, found C, 52.56; H, 6.10; N, 10.71; S, 12.16.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-979882098deb4fb3a3f50d1cb8b34f5e
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07582626B2

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