Potassium Carbonate → 4-[3-[6-(3-Acetyl-5-trifluoromethanesulfonyloxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

HRID 417042Notes

Reaction equation

HRID 417042 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[CH:7]=[C:8]([OH:10])[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:25]([O:27][C:28](=[O:53])[CH2:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]Br)[C:34]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH3:26]>CC(C)=O.CN(C=O)C>[CH2:25]([O:27][C:28](=[O:53])[CH2:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:10][C:8]2[CH:7]=[C:6]([O:11][S:12]([C:15]([F:18])([F:16])[F:17])(=[O:14])=[O:13])[CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=2)[C:34]=1[CH2:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])[CH3:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 575864914-[3-(6-Bromo-hexyl)-2-(ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterHCID 59833966Trifluoro-methanesulfonic acid 3-acetyl-5-hydroxy-phenyl ester

Product 1

HCID 594968454-[3-[6-(3-Acetyl-5-trifluoromethanesulfonyloxy-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 3-acetyl-5-hydroxy-phenyl ester (1.0 g) in a mixture of acetone and DMF (2:1, 80 mL) were added potassium carbonate (2.4 g) and 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.8 g). The resulting mixture was stirred at 75° C. for 3 h. 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 1.7 g of the title compound (72% yield). HRMS calcd for C32H41O10S1F3 [M+H]+ 675.2446, observed 675.2440.

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-16331b2026a24f0cb41dbff6c529271d
Source dataset
uspto-grants-2012_01
Patent number
US08088936B2

Reaction notes

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