(Trifluoromethyl)trimethylsilane → HCID 59536939, compound

HRID 2402783Notes

Reaction equation

[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([Si](C)(C)C)([F:32])[F:31].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:22]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=1)[CH:10]([OH:11])[C:30]([F:32])([F:31])[F:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Of the compound from Example 97A, 300 mg (0.78 mmol) were dissolved in 5 ml of THF, cooled to 0° C., and admixed with 183 μl (1.17 mmol) of (trifluoromethyl)trimethylsilane and then with 39 μl (39 μmol) of a 1M solution of tetra-n-butylammonium fluoride in THF. The cooling bath was removed and the mixture was stirred at RT overnight. Following addition of 2 ml of 1N hydrochloric acid, it was stirred for a further 30 min. The THF was removed on a rotary evaporator and the product was purified by preparative chromatography (Method 10). This gave 168 mg (47% of theory) of the title compound as a diastereomer mixture (ratio about 3:2)

Workup

customThe cooling bath was removed
additionaddition of 2 ml of 1N hydrochloric acid, it
stirringwas stirred for a further 30 min
customThe THF was removed on a rotary evaporator
customthe product was purified by preparative chromatography (Method 10)

Sources & evidence

ORD record: ord-b092408c3c2c4f69b77aea9d25a9e011
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796324B2

Reaction notes

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