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Dimethylformamide → 3-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester

HRID 1181100
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HRID 1181100 반응식
[CH2:1]([O:3][C:4](=C)[CH2:5][CH2:6][C:7]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:8]=1[C:9]#[N:10])[CH3:2].[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)=[N:20][C:19]=1[CH2:36][CH2:37]OS(C1C=CC(C)=CC=1)(=O)=O.CN(C=[O:53])C>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:53])[CH2:5][CH2:6][C:7]1[CH:14]=[CH:13][C:12]([O:15][CH2:37][CH2:36][C:19]2[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:25][CH:24]=3)[O:22][C:18]=2[CH3:17])=[CH:11][C:8]=1[C:9]#[N:10])[CH3:2]
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참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 179843252-(3-Ethoxy-but-3-enyl)-5-hydroxy-benzonitrileHCID 59759494Toluene-4-sulfonic acid 2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethyl ester

생성물 1

HCID 692321723-(2-Cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate
용매

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온도
60 °C

실험 절차

A mixture of 2-(3-ethoxy-but-3-enyl)-5-hydroxy-benzonitrile (220 mg, 1.00 mmol), toluene-4-sulfonic acid 2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethyl ester (450 mg, 1.00 mmol; Preparation 6), and CsCO3 (978 mg, 3.00 mmol) in DMF (10 mL) was stirred overnight at 60° C. under an N2. The mixture was cooled, diluted with EtOAc (20 mL) and washed with brine (20 mL). The organic layer was dried (Na2SO4) and concentrated. The product mixture was purified by radial chromatography (10-70% EtOAc/hexanes) to give 3-(2-cyano-4-{2-[5-methyl-2-(4-phenoxyphenyl)oxazol-4-yl]ethoxy}phenyl)propionic acid ethyl ester (201 mg). A solution of this ester in EtOH (10 mL) and 5N NaOH (10 mL) was heated at 70° C. overnight, concentrated, acidified with 1N HCl, and extracted with EtOAc. The organic layer dried (Na2SO4) and concentrated to give the title compound (192 mg); MS [ES] m/z 469 (M+1).

후처리

  1. temperatureThe mixture was cooled
  2. washwashed with brine (20 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe product mixture was purified by radial chromatography (10-70% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-4fe4c4379d8c41e982f51e8494e310de
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07282501B2

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