Propionic Acid → HCID 59427835, 화합물

HRID 502542

반응식

HRID 502542 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 59427835HCID 59427835, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 57417360Sodium chloride; water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5d18453330c54bf69d0ca83ae9abd1ee
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776868B2

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