Tetrahydrofuran → HCID 57708956, compound

HRID 546973Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[CH3:24][O:25][C:26](=[O:65])[CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([CH2:62][CH3:63])([C:43]3[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]4([O:56][Si](C)(C)C)[CH2:55][CH2:54][CH2:53][CH2:52]4)=[C:45]([CH3:61])[CH:44]=3)[CH2:41][CH3:42])=[CH:36][C:35]=2[CH3:64])[CH:33]=1>>[CH3:24][O:25][C:26](=[O:65])[CH2:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([CH2:41][CH3:42])([C:43]3[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]4([OH:56])[CH2:52][CH2:53][CH2:54][CH2:55]4)=[C:45]([CH3:61])[CH:44]=3)[CH2:62][CH3:63])=[CH:36][C:35]=2[CH3:64])[CH:33]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

HCID 57709185[5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester

Product 1

HCID 57708956HCID 57708956, compoundYield 39.2%

Procedure

A 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.079 mL, 0.079 mmol) was added to [5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid methyl ester (Example 94-(1); 38.2 mg, 0.0656 mmol), and the mixture was stirred for two hours. The reaction mixture was purified by silica gel chromatography (35 to 50% ethyl acetate/hexane) to give the title compound (13.1 mg, 39%).

Workup

customThe reaction mixture was purified by silica gel chromatography (35 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-56f743f998a44c0580f3f9ff0e7a8e76
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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