Triethylamine → HCID 117759767, compound

HRID 1049564Notes

Reaction equation

HRID 1049564 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([CH:24]([CH2:31][CH2:32][OH:33])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:21]=[CH:22][CH:23]=2)=[CH:12][C:11]=1[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36].C(N(CC)CC)C>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([CH:24]([CH2:31][CH:32]=[O:33])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:21]=[CH:22][CH:23]=2)=[CH:12][C:11]=1[CH2:34][C:35]([CH3:36])([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 117759879HCID 117759879, compound

Product 1

HCID 117759767HCID 117759767, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of ethyl 3-(3-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)-5-hydroxypentanoate (330 mg) and triethylamine (0.89 mL) in DMSO (5 mL) was added sulfur trioxide pyridine complex (410 mg), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added, at room temperature, 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product (350 mg) of the title compound as a pale-orange oil. This compound was used for the next step without further purification.

Workup

  1. additionTo the reaction mixture was added, at room temperature
  2. extraction1N hydrochloric acid, and the mixture was extracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-84b37b54c3b740bf9d3fec383d9d3a57
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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