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Potassium Carbonate → 2-(Benzo[1,3]dioxol-5-yloxy)-2-methyl-3-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy)-phenyl)-propionic acid

HRID 348371
ノート
印刷プレビュー

反応式

HRID 348371 の反応式
C([O:3][C:4](=[O:25])[C:5]([O:15][C:16]1[CH:24]=[CH:23][C:19]2[O:20][CH2:21][O:22][C:18]=2[CH:17]=1)([CH3:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10](O)=[CH:9][CH:8]=1)C.[CH3:26][C:27]1[O:31][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)[CH:33]=2)=[N:29][C:28]=1[CH2:43][CH2:44][O:45]S(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(O)C>[O:20]1[C:19]2[CH:23]=[CH:24][C:16]([O:15][C:5]([CH3:14])([CH2:6][C:7]3[CH:12]=[CH:11][C:10]([O:45][CH2:44][CH2:43][C:28]4[N:29]=[C:30]([C:32]5[CH:37]=[CH:36][CH:35]=[C:34]([C:38]6[S:39][CH:40]=[CH:41][CH:42]=6)[CH:33]=5)[O:31][C:27]=4[CH3:26])=[CH:9][CH:8]=3)[C:4]([OH:25])=[O:3])=[CH:17][C:18]=2[O:22][CH2:21]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 693164102-(Benzo[1,3]dioxol-5-yloxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl esterHCID 86593517Toluene-4-sulfonic acid 2-[5-methyl-2-(3-thiophen-2-ylphenyl)oxazol-4-yl]ethyl ester

生成物 1

HCID 103037572-(Benzo[1,3]dioxol-5-yloxy)-2-methyl-3-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy)-phenyl)-propionic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

A mixture of 2-(benzo[1,3]dioxol-5-yloxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl ester (0.030 mmol) (see Ex. 58, Part C), toluene-4-sulfonic acid 2-[5-methyl-2-(3-thiophen-2-ylphenyl)oxazol-4-yl]ethyl ester (0.030 mmol) (see Ex. 5, Part B) and 325 mesh K2CO3 (0.084 g, 0.60 mmol) in ethanol (2 mL) was heated to reflux for 24 h under N2. Aqueous 5N NaOH (0.5 mL) and additional ethanol (1 mL) was added to the reaction mixture and it was heated at reflux for an additional 2 h. The reaction was cooled and the solvent removed in vacuo. The residue was acidified with aqueous 1 N HCl (5 mL), extracted with water and CH2Cl2 and the organic layer dried by passing it through a Varian Chem Elut 1003 cartridge. The solvent was removed in vacuo to give 2-(benzo[1,3]dioxol-5-yloxy)-2-methyl-3-(4-{2-[5-methyl-2-(3-thiophen-2-yl-phenyl)-oxazol-4-yl]-ethoxy}-phenyl)-propionic acid. 1H NMR (400 MHz, CDCl3) δ 8.19 (t, 1H, J=1.71 Hz), 7.85–7.82 (m, 1H), 7.67–7.63 (m, 1H), 7.42 (t, 1H, J=7.82 Hz), 7.38–7.37 (m, 1H), 7.28–7.26 (m, 1H), 7.13 (d, 2H, J=8.79 Hz), 7.06 (dd, 1H, J=4.88 Hz, J=3.42 Hz), 6.79 (d, 2H, J=8.79 Hz), 6.60 (d, 1H, J=8.30 Hz), 6.40 (d, 1H, J=2.44 Hz), 6.32 (dd, 1H, J=8.30 Hz, J=2.44 Hz), 5.87 (d, 2H, J=0.98 Hz), 4.19 (t, 2H, J=6.11 Hz), 3.15 (d, 1H, J=14.17 Hz), 3.04–3.01 (m, 3H), 2.39 (s, 3H), 1.30 (s, 3H);HRMS (ES+) m/z exact mass calcd for C33H30NO7S 584.1743, found 584.1744.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 24 h under N2
  3. temperaturewas heated
  4. temperatureat reflux for an additional 2 h
  5. temperatureThe reaction was cooled
  6. customthe solvent removed in vacuo
  7. extractionextracted with water and CH2Cl2
  8. customthe organic layer dried
  9. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-15e3225a09664b22b502c7c175b215c4
出典データセット
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07176224B2

反応ノート

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