Ethyl Acetate → HCID 69627447, compound

HRID 1743467Notes

Reaction equation

HRID 1743467 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:17]2[CH:18]=[C:19]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=3)[C:20]([OH:30])=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=3)[CH:22]=2)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47].CCOC(C)=O>CN(C=O)C.O>[C:49]([O:48][C:46](=[O:47])[CH2:45][O:30][C:20]1[C:19]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=2)=[CH:18][C:17]([C:15](=[O:16])[NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:22][C:21]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1)([CH3:52])([CH3:51])[CH3:50]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 53695102HCID 53695102, compound

Product 1

HCID 69627447HCID 69627447, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′-hydroxy-3,3″-dimethyl-[1,1′:3′,1″]terphenyl-5′-carboxylic acid (7-phenyl-heptyl)-amide (240 mg, 0.516 mmol) in 2.5 mL anhydrous DMF was added solid K2CO3 (84 mg, 0.613 mmol). The reaction mixture was stirred at room temperature for 2 min before t-butyl bromoacetate (158 mg, 0.812 mmol, 812 μL) was added. The reaction was stirred overnight at room temperature after which point it was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with water to remove DMF. Then they were dried with Na2SO4 and the solvent was removed in vacuo to give an oil that was subjected to flash column chromatography (15% EtOAc: 85% Hexanes) to yield 180 mg, 60% of a colorless oil. 1H NMR (CDCl3) δ 1.25 (s, 9H); 1.25–1.40 (m, 6H); 1.28–1.47 (m, 4H); 2.40 (s, 6H); 2.57 (t, J=8.18 Hz, 2H); 3.43 (quartet, J=8.18 Hz, 2H); 3.73 (s, 2H); 6.06 (t, J=5.73 Hz, 1H); 7.08–7.20 (m, 5H); 7.20–7.32 (m, 4H); 7.37–7.46 (m, 4H); 7.68 (s, 2H).

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with water
  4. customto remove DMF
  5. dry with materialThen they were dried with Na2SO4
  6. customthe solvent was removed in vacuo
  7. customto give an oil that

Sources & evidence

ORD record
ord-93301442a8dd4a27aa28d5b90806233e
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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