(Trifluoromethyl)trimethylsilane → HCID 59722545, compound

HRID 1664846Notes

Reaction equation

HRID 1664846 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[C@H:35]1[CH2:41][N:40]2[C:42]([CH:45]=[O:46])=[CH:43][N:44]=[C:39]2[C@H:38]([NH:47][C:48](=[O:54])[O:49][C:50]([CH3:53])([CH3:52])[CH3:51])[CH2:37][CH2:36]1>>[F:27][C:28]1[C:33]([F:34])=[CH:32][CH:31]=[CH:30][C:29]=1[C@H:35]1[CH2:41][N:40]2[C:42]([CH:45]([OH:46])[C:2]([F:4])([F:3])[F:1])=[CH:43][N:44]=[C:39]2[C@H:38]([NH:47][C:48](=[O:54])[O:49][C:50]([CH3:52])([CH3:51])[CH3:53])[CH2:37][CH2:36]1

Participants

4

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 59722730HCID 59722730, compound

Product 1

HCID 59722545HCID 59722545, compoundYield 66.2%

Procedure

(Trifluoromethyl)trimethylsilane (0.5 M in tetrahydrofuran; 2.15 mL, 1.07 mmol) and tetrabutylammonium fluoride (1.0 M in tetrahydrofuran; 0.107 mL, 0.107 mmol) were sequentially added to neat tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-formyl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (0.14 g, 0.36 mmol). After 15 min, the reaction mixture was quenched with saturated sodium bicarbonate. The mixture was extracted with dichloromethane (3×), and the combined organic extracts were washed with water, saturated brine, dried over sodium sulfate, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (110 mg). MS 462.1 (M+1).

Workup

  1. customthe reaction mixture was quenched with saturated sodium bicarbonate
  2. extractionThe mixture was extracted with dichloromethane (3×)
  3. washthe combined organic extracts were washed with water, saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-02e93846803b4f3e95b7c08d71de7c02
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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