Potassium tert-butoxide → HCID 178437374, compound

HRID 925930Notes

Reaction equation

[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH:15]=[C:16]([C:18]#[C:19][Si](C)(C)C)[N:17]=2)=O)=[C:8]([CH3:24])[C:7]([O:25][CH3:26])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH3:26][O:25][C:7]1[C:8]([CH3:24])=[C:9]2[C:4]([C:1]([OH:3])=[CH:2][C:11]([C:13]3[S:14][CH:15]=[C:16]([C:18]#[CH:19])[N:17]=3)=[N:10]2)=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of compound 208b (8.71 g, 1 eq.) in tert-butanol (240 mL) was added potassium tert-butoxide (5.32 g, 2.1 eq.). The heterogeneous mixture was stirred and heated to 80° C. The solvent was then evaporated and water was added to the resulting black residue. The pH of the mixture was brought to 6 with 1N HCl. The mixture was extracted with dichloromethane. The organic layer was dried over Na2SO4, filtered, and concentrated under vacuo. The solid was purified by chromatography on silica gel to give compound 209b as an orange solid in 52% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.45 (s, 3H), 3.25 (s, 1H), 3.99 (s, 3H), 6.89 (br s, 1H), 7.06 (d, J=9.09 Hz, 1H), 7.72 (s, 1H), 8.26 (d, J=9.09 Hz, 1H), 9.50 (br s, 1H); MS (ESI, EI+): m/z=297 (MH+).

Workup

customThe solvent was then evaporated
additionwater was added to the resulting black residue
extractionThe mixture was extracted with dichloromethane
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuo
customThe solid was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-ed1742d2fbae426f99103fe32eb661ac
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284307B2

Reaction notes

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