Ethylene Glycol → 2-Hydroxyethyl 4-chloro-2-((2-furylmethyl)amino)-5-sulfamoylbenzoate

HRID 1180624ノート

反応式

HRID 1180624 の反応式
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:10]([Cl:21])[CH:9]=2)[O:4][CH:5]=1.[CH2:22](O)[CH2:23][OH:24].CN(C=O)C.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:21][C:10]1[C:11]([S:17](=[O:19])(=[O:18])[NH2:20])=[CH:12][C:13]([C:14]([O:16][CH2:22][CH2:23][OH:24])=[O:15])=[C:8]([NH:7][CH2:6][C:3]2[O:4][CH:5]=[CH:1][CH:2]=2)[CH:9]=1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 3440FurosemideHCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

生成物 1

HCID 589797872-Hydroxyethyl 4-chloro-2-((2-furylmethyl)amino)-5-sulfamoylbenzoate収率 24%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒2 回HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

To a solution of furosemide (OnBio, Canada, 5.2 g, 15.6 mmol) in a mixture of CH2Cl2/DMF (15 mL /20 mL) was added ethylene glycol (Aldrich, Wis., U.S., 4.4 mL, 78.0 mmol) and DMAP (377.5 mg, 3.1 mmol). A solid formed upon the addition of the DMAP and additional DMF (15 mL) was added followed by EDAC (3.9 g, 20.3 mmol). The reaction mixture was allowed to stir at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue redissolved in CH2Cl2 (100 mL). The sample was washed with H2O (3×50 mL), brine, and the sample dried (MgSO4). The residue after evaporation was chromatographed on silica gel eluting with 1:1 hexanes/EtOAc to give the title compound (1.4 g, 24% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.45-8.43 (m, 2H), 7.64 (s, 1H), 7.35 (s, 2H), 7.09 (s, 1H), 6.42-6.41 (m, 1H), 6.37-6.36 (m, 1H), 4.92 (t, J=5.4 Hz, 1H), 4.60 (d, J=5.8 Hz, 2H), 4.28 (br t, 2H), 3.71-3.65 (m, 2H). Mass Spectrum (API-TIS) m/z 375 (MH+).

後処理

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue redissolved in CH2Cl2 (100 mL)
  4. washThe sample was washed with H2O (3×50 mL), brine
  5. dry with materialthe sample dried (MgSO4)
  6. customThe residue after evaporation
  7. customwas chromatographed on silica gel eluting with 1:1 hexanes/EtOAc

出典と根拠

ORDレコード
ord-d72ed42ef564460aa7cd90706c2a9289
出典データセット
uspto-grants-2007_10
特許番号
US07282519B2

反応ノート

読み込み中…