Lithium Hydroxide → 2-(5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetic Acid

HRID 1966897

Reaktionsgleichung

Reaktionsgleichung von HRID 1966897
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[S:19][C:18]([CH2:20][C:21]([O:23]CC)=[O:22])=[N:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Li+].[OH-]>C1COCC1>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[S:19][C:18]([CH2:20][C:21]([OH:23])=[O:22])=[N:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 53323731Ethyl 2-(5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetate

Produkt 1

HCID 533223732-(5-(4-Acetamidophenylsulfonamido)-1,3,4-thiadiazol-2-yl)acetic AcidAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of compound 118E (128 mg, 0.33 mmol) in THF (15 mL) was added 0.1 M aqueous LiOH (3.75 mL) and the mixture was stirred at room temperature. After 24 h, the resultant solution was acidified to pH 4 and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water (20 mL) and concentrated to give the crude product, which was further purified by chromatography on 70-230 mesh silica gel eluted with CH2Cl2:methanol:water 40:10:1 to afford 104 mg (0.29 mmol, 88%) of the product as a solid, mp 206-207° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.05 (s, 3H), 3.81 (s, 2H), 7.65 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 24.8, 37.3, 119.0, 127.5, 137.9, 142.6, 153.3, 169.4, 169.5, 170.9; MS (LCQ, ESI+) Calcd for C12H13N4O5S2 357.0, found 357.0 (M+H)+; HRMS (ESI+, m/z) Calcd for C12H13N4O5S2 357.0327, found 357.0326 (M+H)+.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed with water (20 mL)
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas further purified by chromatography on 70-230 mesh silica gel
  6. washeluted with CH2Cl2:methanol:water 40:10:1

Quellen und Nachweise

ORD-Eintrag
ord-fe1b4f4861174d719ec35ca93ec735a1
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420678B2

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