Tetrabutylammonium Fluoride → HCID 67235617, compound

HRID 69095Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[S:16][C:17]([C:22](C)(C)[O:23][SiH2]C(C)(C)C)=[C:18]([O:20][CH3:21])[CH:19]=2)=[CH:9][C:8]=1[F:31])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:31][C:8]1[CH:9]=[C:10]([O:13][CH2:14][C:15]2[S:16][C:17]([CH2:22][OH:23])=[C:18]([O:20][CH3:21])[CH:19]=2)[CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:32]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-{4-[5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methoxy-thiophen-2-ylmethoxy]-2-fluoro-phenyl}-propionicacid ethyl ester (0.5 g, 1.0 mmol) in THF (5 mL) is added tetra-n-butylammoniumfluoride (1M solution in THF, 2 mL, 2.0 mmol) at 0° C. and the reaction mixture is stirred for 30 minutes at 25° C. The reaction mixture is quenched with water and evaporated to a residue. The residue is extracted with EtOAc, washed with water (15 mL) and brine (15 mL), dried over sodium sulfate, filtered, and concentrated to give the title compound (0.4 g,). 1H NMR (400 MHz, DMSO d6) δ7.41 (s, 1H), 7.19-7.15 (t, J=8.8 Hz, 1H), 6.85-6.75 (m, 2H), 5.32 (br, 1H), 4.85 (s, 2H), 4.55 (s, 2H), 4.04-4.00 (q, J=7.2 Hz, 2H), 3.75 (s, 3H), 3.58 (s, 1H) 3.16-3.12 (t, J=15.2 Hz, 3H), 2.79-2.76 (t, J=14.8 Hz, 2H), 2.55-2.51 (t, J=15.2 Hz, 2H), 1.28-1.22 (t, J=7.2 Hz, 3H),

Workup

customThe reaction mixture is quenched with water
customevaporated to a residue
extractionThe residue is extracted with EtOAc
washwashed with water (15 mL) and brine (15 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2dc53f1c2b644c149812eb08354f72f4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822486B2

Reaction notes

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