Lithium hydroxide, monohydrate → (7-Methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid

HRID 1516024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516024
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[NH:11][C:10]2[S:12][CH:13]=[C:14]([CH2:15][O:16][CH2:17][O:18][CH3:19])[C:9]=2[S:8](=[O:21])(=[O:20])[N:7]=1)C.O.[OH-].[Li+]>O1CCCC1.O>[CH3:19][O:18][CH2:17][O:16][CH2:15][C:14]1[C:9]2[S:8](=[O:21])(=[O:20])[N:7]=[C:6]([CH2:5][C:4]([OH:22])=[O:3])[NH:11][C:10]=2[S:12][CH:13]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 58000246(7-Methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 58000269(7-Methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1lambda6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acidAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of (7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester (0.54 g, 1.55 mmol) in tetrahydrofuran (5 mL) and water (5 mL) was added lithium hydroxide monohydrate (0.33 g, 7.75 mmol). The reaction was stirred at 25° C. for 1 h before it was cooled to 0° C. The reaction was quenched via the addition of 6.0 M aqueous hydrochloric acid solution until a pH of 1-2 was reached. The resulting mixture was extracted with ethyl acetate (3×10 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the crude product, (7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid (0.39 g, 1.21 mmol, 78%), which was used in the next step without further purification.

Aufarbeitung

  1. temperaturewas cooled to 0° C
  2. customThe reaction was quenched via the addition of 6.0 M aqueous hydrochloric acid solution until a pH of 1-2
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×10 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ea8560ccdbbd410f92f3e5c03150c0af
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222404B2

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