Ethylenediamine diacetate → HCID 86644295, 화합물

HRID 2197673

반응식

HRID 2197673 반응식
[O:1]=[C:2]1[CH2:6][S:5][C:4](=[S:7])[N:3]1[CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]1.[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19].C(O)(=O)C.C(O)(=O)C.C(N)CN>C(O)C.C(OCC)(=O)C>[CH2:17]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[O:31][C:30]([CH:32]=[C:6]3[S:5][C:4](=[S:7])[N:3]([CH:8]4[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=[O:15])[CH2:9]4)[C:2]3=[O:1])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH:18]([CH3:20])[CH3:19]

참가 물질

6

반응물 3

HCID 10154317Ethylenediamine diacetateHCID 594462253-(4-Oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acidHCID 59446226HCID 59446226, 화합물

생성물 1

HCID 86644295HCID 86644295, 화합물수율 72%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3-(4-oxo-2-thioxo-thiazolidin-3-yl)-cyclohexanecarboxylic acid (0.075 g, 0.29 mmol), 5-(4-isobutyl-phenyl)-furan-2-carbaldehyde (0.069 g, 0.30 mmol) and ethylenediamine diacetate (0.057 g, 0.32 mmol) in anhydrous ethanol (12 mL) was stirred 30 h at ambient temperature. The reaction mixture was diluted with ethyl acetate (250 mL) and extracted with 0.6 N aq. sodium hydrogensulfite (2×50 mL). The organic layer was separated, dried over sodium sulfate and concentrated. The residue was triturated with hot acetonitrile (5 mL) and allowed to cool to room temperature. The product was filtered off, washed on the funnel with acetonitrile (0.5 mL) and dried in a vacuum oven at 60° C. for 17 h to afford 3-{5-[1-[5-(4-isobutyl-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-yl}-cyclohexanecarboxylic acid (98 mg, 72%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 0.88 (6H, d, J=6.4 Hz), 1.16-1.45 (2H, m), 1.68 (1H, m), 1.84-1.92 (4H, m), 2.25-2.54 (3H, m), 4.98 (1H, m), 7.27 (1H, d, J=3.6 Hz), 7.36 (2H, m), 7.36 (1H, d, J=3.6 Hz), 7.58 (1H, s), 7.77 (2H, m), 12.22 (1H, s). LC/MS: APCI 469.51, HPLC 100%.

후처리

  1. extractionextracted with 0.6 N aq. sodium hydrogensulfite (2×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with hot acetonitrile (5 mL)
  6. temperatureto cool to room temperature
  7. filtrationThe product was filtered off
  8. washwashed on the funnel with acetonitrile (0.5 mL)
  9. customdried in a vacuum oven at 60° C. for 17 h

출처 및 근거

ORD 기록
ord-578468d40da141f28f3d10ed92b038b6
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

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