Tetrabutylammonium Fluoride → HCID 68548121, compound

HRID 470907Notes

Reaction equation

HRID 470907 reaction equation
[S:1](=[O:38])(=[O:37])([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([C@H:15]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[C:29]([Cl:35])[C:28]=3[CH3:36])[C@@H:16]([O:18][Si](C(C)(C)C)(C)C)[CH3:17])=[N:13][N:14]=2)=[CH:6][CH:5]=1)[NH2:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[S:1](=[O:38])(=[O:37])([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:11][C:12]([C@H:15]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[C:29]([Cl:35])[C:28]=3[CH3:36])[C@@H:16]([OH:18])[CH3:17])=[N:13][N:14]=2)=[CH:8][CH:9]=1)[NH2:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68551362HCID 68551362, compound

Product 1

HCID 68548121HCID 68548121, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a pre-cooled (0° C.) solution of 4-(5-((1R,2S)-2-(tert-butyldimethylsilyloxy)-1-(3-chloro-4-cyano-2-methylphenylamino)propyl)-1,3,4-oxadiazol-2-yl)phenyl sulfamate (190 mg, 0.422 mmol) in THF (20 mL) was added TBAF (0.63 mL, 0.63 mmol, 1 M solution in THF) dropwise. The mixture was allowed to warm to room temperature and stirred for two hours, whereupon, concentration under reduced pressure furnished a yellow oil (195 mg). The resulting residue was taken up in EtOAc (60 mL) and washed with H2O (20 mL). The biphasic mixture was separated and the aqueous layer extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provide a yellow oil, which was purified by flash chromatography over silica gel [Dichloromethane-Methanol (7:1) as eluent] to provide the title compound as a white solid (0.032 g, 16%). The resulting solid was diluted with CH2Cl2 (30 mL) and hexanes (70 mL) was added. Upon concentration of the suspension a white solid was provided (1.02 g, 35%). 1H NMR (400 MHz, Acetone d6, δ in ppm) 8.2 (d, J=8.8 Hz, 2 H), 7.99 (d, J=9 Hz, 2H), 7.47 (d, J=9 Hz, 1H), 6.86 (d, J=9 Hz, 1 H), 5.64 (d, J=8 Hz, 1 H), 5.18-5.15 (m, 1 H), 4.81 (br s, 1 H), 4.63 (br s, 1 H), 2.40 (s, 3 H), 1.40 (d, J=7 Hz, 3 H).

Workup

  1. concentrationwhereupon, concentration under reduced pressure

Sources & evidence

ORD record
ord-ff76d676f8ce47d4b0bb8a8facdbad83
Source dataset
uspto-grants-2014_01
Patent number
US08629167B2

Reaction notes

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