Tetrahydrofuran → HCID 57709131, compound

HRID 547090Notes

Reaction equation

HRID 547090 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.C[O:25][C:26](=[O:63])[CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([CH2:60][CH3:61])([C:43]3[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]4([OH:58])[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]4)=[C:45]([CH3:59])[CH:44]=3)[CH2:41][CH3:42])=[CH:36][C:35]=2[CH3:62])[CH:33]=1.C(=O)(O)[O-].[Na+]>>[CH2:41]([C:40]([C:37]1[CH:38]=[CH:39][C:34]([C:32]2[CH:33]=[C:28]([CH2:27][C:26]([OH:63])=[O:25])[CH:29]=[N:30][CH:31]=2)=[C:35]([CH3:62])[CH:36]=1)([C:43]1[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]2([OH:58])[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)=[C:45]([CH3:59])[CH:44]=1)[CH2:60][CH3:61])[CH3:42]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 67065080HCID 67065080, compound

Product 1

HCID 57709131HCID 57709131, compoundYield 32.4%

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 mL, 1.0 mmol) was added to the mixture containing [5-(4-{1-ethyl-1-[4-(1-hydroxy-cycloheptylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester (32.0 mg), and the mixture was stirred at room temperature for 15 minutes. The mixture was further stirred with microwave heating at 100° C. for five minutes. A sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was purified by high performance liquid chromatography (Shiseido CAPCELL PAK C18 MGII, 20 mm I.D.×50 mm, methanol:20 mM ammonium acetate solution=55:45 to 100:0, mL/min). A sodium bicarbonate solution was added to the eluate, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure to give the target compound as a colorless oil (10.1 mg, 22% in two steps).

Workup

  1. stirringThe mixture was further stirred with microwave
  2. temperatureheating at 100° C. for five minutes
  3. extractionfollowed by extraction with ethyl acetate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by high performance liquid chromatography (Shiseido CAPCELL PAK C18 MGII, 20 mm I.D
  6. additionA sodium bicarbonate solution was added to the eluate
  7. extractionfollowed by extraction with ethyl acetate
  8. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1070978ea35a46b8a63608a0fa2e66cf
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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