Bromotrimethylsilane → HCID 59317166, compound

HRID 389902Notes

Reaction equation

Br[Si](C)(C)C.[P:6]([O:39]CC)([O:36]CC)([O:8][CH2:9][C@@:10]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:14](=[O:15])[N:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=2)[C:12](=[O:28])[N:11]1[CH3:29])=[O:7]>C(Cl)Cl>[P:6]([OH:39])([OH:36])([O:8][CH2:9][C@@:10]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:14](=[O:15])[N:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([C:24]([F:27])([F:25])[F:26])[CH:17]=2)[C:12](=[O:28])[N:11]1[CH3:29])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Under argon atmosphere, 2.5 mL of bromotrimethylsilane is added to a solution of 0.80 g of (S)-[1-(4-cyano-3-trifluoromethylphenyl)-2,5-dioxo-3-methyl-4-phenylimidazolidin-4-yl]methyl diethyl phosphate in 25 mL of DCM cooled at 0° C. The reaction is stirred for 1 hour at 0° C. then 18 hours at room temperature. The solvent is evaporated then the residue is dissolved in a mixture of water and methanol. Solvents are evaporated and this process repeated twice. The crude product is purified by chromatography over silica gel while eluting with 90/10/1/1 to 85/15/2/2 dichloromethane/methanol/acetic acid/water mixture to provide the desired compound.

Workup

custom18 hours
customat room temperature
customThe solvent is evaporated
dissolutionthe residue is dissolved in a mixture of water and methanol
customSolvents are evaporated
customThe crude product is purified by chromatography over silica gel
washwhile eluting with 90/10/1/1 to 85/15/2/2 dichloromethane/methanol/acetic acid/water mixture

Sources & evidence

ORD record: ord-992609020e7742eb95e18f9b0d069051
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383608B2

Reaction notes

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