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

HRID 1661803ノート

反応式

HRID 1661803 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5c6bba162fc84fd2b3ab985e969cc5c6
出典データセット
uspto-grants-2011_10
特許番号
US08030305B2

反応ノート

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