Lithium Hydroxide → (7-Methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl)-acetic acid

HRID 424226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424226
C([O:3][C:4](=[O:23])[CH2:5][C:6]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:15][C:9]=2[S:8](=[O:22])(=[O:21])[CH:7]=1)C.[OH-].[Li+]>CO>[CH3:20][S:17]([NH:16][C:14]1[CH:13]=[CH:12][C:10]2[NH:11][C:6]([CH2:5][C:4]([OH:23])=[O:3])=[CH:7][S:8](=[O:21])(=[O:22])[C:9]=2[CH:15]=1)(=[O:18])=[O:19]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 59853588(7-Methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 59853605(7-Methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,4]thiazin-3-yl)-acetic acidAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,4]thiazin-3-yl)-acetic acid ethyl ester (prepared as described in US patent application US 2008/0031852, 600 mg, 1.666 mmol) in methanol (30 mL) was cooled to 0° C. in an ice-water bath and treated with 2.0 M aqueous lithium hydroxide solution (4.17 mL, 8.332 mmol). The reaction mixture was allowed to warm to 25° C. and stirred for 1 h. The methanol was removed in vacuo and the reaction mixture was poured into 0.5 M aqueous hydrochloric acid solution (20 mL) on ice, extracted with ethyl acetate (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford an orange solid. The crude solid was triturated with diethyl ether to afford the desired product, (7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,4]thiazin-3-yl)-acetic acid (409 mg, 1.232 mmol, 73.9%), as a yellow solid. LC-MS calcd for C11H12N2O6S2 332.4, found 333.0 [M+H+].

Aufarbeitung

  1. customThe methanol was removed in vacuo
  2. additionthe reaction mixture was poured into 0.5 M aqueous hydrochloric acid solution (20 mL) on ice
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford an orange solid
  8. customThe crude solid was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-94d8f55865ec4179962734124565a0b9
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101800B2

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