Propionic Acid → HCID 59427835、化合物

HRID 502542ノート

反応式

HRID 502542 の反応式
C(O)(=[O:4])CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:25]([CH2:28]C)[CH2:26][CH3:27])C.[NH2:30][C:31]1[S:32][C:33]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:34]([CH3:41])[C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH2:45]([O:44][C:42]([C:33]1[S:32][C:31]([NH:30][C:28]([NH:25][CH2:26][CH3:27])=[O:4])=[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:34]=1[CH3:41])=[O:43])[CH3:46]

参加物

7

反応物 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 78537Diethyl 5-amino-3-methylthiophene-2,4-dicarboxylateHCID 199401P,P-Diphenylphosphinic azide

生成物 1

HCID 59427835HCID 59427835、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of propionic acid (0.8 ml, 10 mol), diphenylphosphoryl azide (2.22 ml, 10.3 mmol) and triethylamine (1.39 ml, 10 mmol) in toluene (15 ml) was refluxed for 90 minutes. The mixture was then cooled to below 40° C., and a solution of ethyl 2-amino-5-(ethoxycarbonyl)-4-methylthiophene-3-carboxylate (1.76 g, 6.85 mmol) in toluene (10 ml) was added, the mixture refluxed for 24 hours. The reaction mixture was diluted with brine, and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. Solvent was removed under reduced pressure, and the residue purified by column chromatography, eluting with ethyl acetate/hexane 1:6 to 1:4, to provide ethyl 5-(ethoxycarbonyl)-2-[(ethylamino)carbonylamino]-4-methylthiophene-3-carboxylate. The structure was confirmed by 1H NMR and mass spectrometry.

後処理

  1. temperaturewas refluxed for 90 minutes
  2. temperatureThe mixture was then cooled to below 40° C.
  3. temperaturethe mixture refluxed for 24 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customSolvent was removed under reduced pressure
  8. customthe residue purified by column chromatography
  9. washeluting with ethyl acetate/hexane 1:6 to 1:4

出典と根拠

ORDレコード
ord-5d18453330c54bf69d0ca83ae9abd1ee
出典データセット
uspto-grants-2010_08
特許番号
US07776868B2

反応ノート

読み込み中…