Methanol → HCID 21911993, compound

HRID 2207307Notes

Reaction equation

S([CH2:11][N+:12]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CC(C)([O-])C.[K+].[CH3:20][Si:21]([CH3:34])([CH3:33])[CH2:22][CH2:23][O:24][CH2:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH:31]=O.CO>COCCOC.O>[CH3:20][Si:21]([CH3:34])([CH3:33])[CH2:22][CH2:23][O:24][CH2:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH2:31][C:11]#[N:12]

Participants

Conditions

Temperature: -60 °C

Procedure

1.73 g (8.84 mmol) tosylmethylisocyanide were solved in 10 ml DME and cooled down to −60° C. At this temperature first 1.98 g potassium tert-butoxide was added then slowly a solution of 2.00 g (8.84 mmol) 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde in 5 ml DME. After 2 hours stirring at −60° C. the reaction was allowed to reach 0° C. and 5 ml methanol (123.60 mmol) was added to the solution. The reaction was stirred for further 24 hours at ambient temperature and for 2 hours at 40° C. Excess water was added and the solution was extracted 3 times with dichloromethane. The organic phase was dried over Na2SO4, after evaporation of the solvent under reduced pressure the raw material was purified by reverse phase column chromatography (water 0.1% TFA/acetonitrile=80/20 to yield 0.87 g (0.367 mol) of the SEM-protected imidazole-acetonitrile.

Workup

customto reach 0° C.
stirringThe reaction was stirred for further 24 hours at ambient temperature and for 2 hours at 40° C
extractionthe solution was extracted 3 times with dichloromethane
dry with materialThe organic phase was dried over Na2SO4
customafter evaporation of the solvent under reduced pressure the raw material
customwas purified by reverse phase column chromatography (water 0.1% TFA/acetonitrile=80/20

Sources & evidence

ORD record: ord-4cf27ae5173a4c0c9fc1f6e67ee26887
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376432B2

Reaction notes

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