Cesium carbonate → 4-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

HRID 417048Notes

Reaction equation

HRID 417048 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH:13]=[C:14]([OH:16])[CH:15]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:28]([O:30][C:31](=[O:56])[CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]Br)[C:37]=1[CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH3:29]>CC(C)=O.CN(C=O)C>[CH2:28]([O:30][C:31](=[O:56])[CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][O:16][C:14]2[CH:13]=[C:12]([C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[CH:11]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH:15]=2)[C:37]=1[CH2:49][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH3:29]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 594968091-(3-Benzo[1,3]dioxol-5-yl-5-hydroxy-phenyl)-2-methyl-propan-1-one

Product 1

HCID 594968284-[3-[6-(3-Benzo[1,3]dioxol-5-yl-5-isobutyryl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterYield 75%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-(3-benzo[1,3]dioxol-5-yl-5-hydroxy-phenyl)-2-methyl-propan-1-one (109 mg) in a mixture of acetone and DMF (2:1, 3 mL) were added cesium carbonate (624 mg) and 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (190 mg). The resulting mixture was stirred at 75° C. overnight. Then the insoluble material was filtered out and the filtrate was diluted with ethyl acetate and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield 194 mg of the title compound (75% yield). HRMS calcd for C40H50O9 [M+Na]+ 697.3347, observed 697.3344.

Workup

  1. filtrationThen the insoluble material was filtered out
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified on a silica gel column

Sources & evidence

ORD record
ord-f225f5aa6eb948aaab79b1b46094a556
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

Loading…