Sodium hydride → ({2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl ester

HRID 2305345

Reaktionsgleichung

Reaktionsgleichung von HRID 2305345
[H-].[Na+].[OH:3][CH:4]([C:22]1[CH:30]=[C:29]([O:31][CH3:32])[C:25]2[O:26][CH2:27][O:28][C:24]=2[CH:23]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])(=[O:13])=[O:12].Br[CH2:34][C:35]([O:37][CH3:38])=[O:36]>O1CCCC1>[CH3:38][O:37][C:35](=[O:36])[CH2:34][N:14]([S:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH:4]([OH:3])[C:22]1[CH:30]=[C:29]([O:31][CH3:32])[C:25]2[O:26][CH2:27][O:28][C:24]=2[CH:23]=1)(=[O:12])=[O:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 186155802-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamide

Produkt 1

HCID 22965597({2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl esterAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sixty percent sodium hydride suspension in oil (0.422 g, 10.55 mmol) was washed with tetrahydrofuran and was added to tetrahydrofuran (175 mL). To this was added 2-[hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-N-o-tolyl-benzenesulfonamide (4.1 g, 9.59 mmol). After stirring for 30 minutes, methyl bromoacetate (1.09 mL, 11.5 mmol) was added followed by stirring at reflux for 18 hours. The mixture was evaporated to an oil in vacuo, and the residue was resuspended in ethyl ether, washed with 1N citric and brine. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to a solid. The material was chromatographed on 300 g silica gel eluted with a mixture of ethyl acetate and hexane (35:65). The appropriate fractions were concentrated in vacuo from ethyl ether giving a solid, 4.29 g, 89.5% yield. NMR spectra and elemental analysis were consistent with the structure.

Aufarbeitung

  1. stirringby stirring
  2. temperatureat reflux for 18 hours
  3. customThe mixture was evaporated to an oil in vacuo
  4. washwashed with 1N citric
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to a solid
  8. customThe material was chromatographed on 300 g silica gel
  9. washeluted with a mixture of ethyl acetate and hexane (35:65)
  10. concentrationThe appropriate fractions were concentrated in vacuo from ethyl ether giving a solid, 4.29 g, 89.5% yield

Quellen und Nachweise

ORD-Eintrag
ord-13e77e7af2c142ad98575f04f8f343cd
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06440962B2

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