Hydrochloric Acid → 4-{3E-[4-(1-Carboxy-1-methyl-ethoxy)-2-methoxy-5-thiophen-2-yl-phenyl]-acryloyl}-benzoic acid

HRID 10668

반응식

HRID 10668 반응식
[CH:1]([C:3]1[C:15]([O:16][CH3:17])=[CH:14][C:6]([O:7][C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])=[C:5]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[CH:4]=1)=O.[C:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)(=[O:25])[CH3:24].C[O-].[Li+].Cl>CN(C)C=O.CO.O>[C:9]([C:8]([CH3:13])([O:7][C:6]1[C:5]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)=[CH:4][C:3](/[CH:1]=[CH:24]/[C:23]([C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)=[O:25])=[C:15]([O:16][CH3:17])[CH:14]=1)[CH3:12])([OH:11])=[O:10]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 114704-Acetylbenzoic AcidHCID 4177230Lithium methanolateHCID 219809942-(4-Formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid

생성물 1

HCID 101518134-{3E-[4-(1-Carboxy-1-methyl-ethoxy)-2-methoxy-5-thiophen-2-yl-phenyl]-acryloyl}-benzoic acid수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 21901440N,N-dimethylformamide methanol용매

실험 절차

2-(4-Formyl-5-methoxy-2-thiophen-2-yl-phenoxy)-2-methyl-propionic acid (Ex-47, 0.23 g, 0.72 mmol) and 4-acetylbenzoic acid (0.12 g, 0.72 mmol) were dissolved in a dimethylformamide-methanol solution (5 mL, 7:3). After complete dissolution, lithium methoxide (0.11 g, 2.9 mmol) was added and the resulting orange slurry was stirred in the dark at room temperature for 4 h. Upon completion, as determined by HPLC, the mixture was diluted with water (15 mL), acidified with a 1 N hydrochloric acid solution, and extracted with ethyl acetate (4×25 mL). The combined organic extracts were dried over sodium sulfate and evaporated to dryness. The crude oil was taken up in a tetrahydrofuran-heptane solution (5 mL, 10:1) and warmed to 60° C. to obtain complete dissolution and allowed to cool to room temperature. The resulting precipitate was collected on filter paper and dried in vacuo to yield 0.30 g (90%) of the title compound as a dark yellow solid, mp 135–137° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.32 (s, 1H), 8.23 (d, 2H, J=8.4 Hz), 8.10 (d, 2H, J=8.4 Hz), 7.99 (d, 2H, J=15.6 Hz), 7.71 (d, 1H, J=3.0 Hz), 7.54 (d, 1H, J=5.1 Hz), 7.14 (dd, 1H, J=5.1, 3.0 Hz), 6.49 (s, 1H), 3.85 (s, 3H), 1.69 (s, 6H). MS (ESI) m/z=467 ([M+H]+, 100%). Anal. Calcd. for C25H28O8S.EtOH: C, 63.27; H, 5.51; S, 6.26. Found: C, 63.40; H, 5.19; S, 6.38.

후처리

  1. additionwas added
  2. extractionextracted with ethyl acetate (4×25 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. customevaporated to dryness
  5. temperaturewarmed to 60° C.
  6. customto obtain complete
  7. dissolutiondissolution
  8. temperatureto cool to room temperature
  9. customThe resulting precipitate was collected
  10. filtrationon filter paper
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-92412a7fd2494c52aa9756f44c45fa54
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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