Ethanol → (2-Amino-benzothiazol-6-yl)-acetic acid ethyl ester

HRID 1661803

Reaktionsgleichung

Reaktionsgleichung von HRID 1661803
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH2:11][C:12]([OH:14])=[O:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:15](O)[CH3:16]>OS(O)(=O)=O>[CH2:15]([O:13][C:12](=[O:14])[CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH2:1])[S:3][C:4]=2[CH:10]=1)[CH3:16]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 757163(2-Aminobenzothiazol-6-yl)acetic acid

Produkt 1

HCID 821202(2-Amino-benzothiazol-6-yl)-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Versuchsvorschrift

A solution of (2-amino-benzothiazol-6-yl)-acetic acid (0.61 mmol, as prepared by Meyer et al. in J. Med. Chem. 1997, 40, 1060) in absolute ethanol (10 mL) was treated with 3 drops of concentrated H2SO4 and ca. 1 g of dry 4A molecular sieves, and heated to reflux for 3 d. The reaction was concentrated to dryness in vacuo, partitioned between CH2Cl2 and saturated aqueous NaHCO3, filtered, and phases separated. The aqueous layer was extracted with CH2Cl2, and the combined organic layers were washed with water and brine, dried over Na2SO4, filtered, and the filtrate concentrated in vacuo giving the title compound as a yellow solid. 1H NMR (CDCl3) δ 7.50 (1H, m), 7.41 (1H, d, J=8.3 Hz), 7.20 (1H, dd, J=8.2 Hz, 1.9 Hz), 4.15 (2H, q, J=7.2 Hz), 3.65 (2H, s), 3.42 (4H, s [NH2+H2O]), 1.26 (3H, t, J=7.1 Hz). ESI-MS (m/z): Calcd for C11H12N2O2S: 236.1; found 237.1 (M+H).

Aufarbeitung

  1. dry with materialof dry 4A molecular sieves
  2. temperatureheated
  3. temperatureto reflux for 3 d
  4. concentrationThe reaction was concentrated to dryness in vacuo
  5. custompartitioned between CH2Cl2 and saturated aqueous NaHCO3
  6. filtrationfiltered
  7. customphases separated
  8. extractionThe aqueous layer was extracted with CH2Cl2
  9. washthe combined organic layers were washed with water and brine
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5c6bba162fc84fd2b3ab985e969cc5c6
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030305B2

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