Tetrabutylammonium Fluoride → HCID 57665506, compound

HRID 2358429Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:33])[NH:13][C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[C:18]([C:27]#[C:28][Si](C)(C)C)[CH:17]=2)[CH3:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:33])[NH:13][C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:24])=[O:25])=[C:18]([C:27]#[CH:28])[CH:17]=2)[CH3:15])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

(R)—N-(4-{1-[3-(4-tert-Butyl-phenyl)ureido]ethyl}-2-trimethylsilanylethynyl-phenyl)methanesulfonamide (11 mg, 0.023 mmol) was dissolved in THF. The reaction mixture was cooled down to 0° C. 1.0 M solution of tetrabutylammoniumfluoride in THF (0.068 ml, 0.068 mmol, 3 eq.) was added into the reaction mixture. The reaction mixture was stirred for 1.5 hrs. The reaction mixture was concentrated in vacuo and purified with column chromatography (n-Hx:EA=1:1) to yield title compound (7.0 mg, 74%) as a solid.

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified with column chromatography (n-Hx:EA=1:1)

Sources & evidence

ORD record: ord-ea6a8d301cd54a409e814e6e90628a95
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763657B2

Reaction notes

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