N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → HCID 59238323, compound

HRID 220174Notes

Reaction equation

HRID 220174 reaction equation
[C:1]([O:5][C:6](=[O:46])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:45])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:35](=[O:44])[NH:36][C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)[CH2:25][CH2:26][O:27][Si](C(C)(C)C)(C)C)=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.F.F.[F-]>C1COCC1>[C:1]([O:5][C:6](=[O:46])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:45])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:35](=[O:44])[NH:36][C:37]2[CH:38]=[CH:39][C:40]([Br:43])=[CH:41][CH:42]=2)[CH2:25][CH2:26][OH:27])=[CH:20][CH:19]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)HCID 59238282(E)-[2-(3-{4-[1-(4-Bromo-phenylcarbamoyl)-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 59238323HCID 59238323, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-[2-(3-{4-[1-(4-bromo-phenylcarbamoyl)-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (1.6 g, 2.26 mmol) in THF (40 mL) was added tetrabutylammonium dihydrogen trifluoride (1.36 g, 4.52 mmol). This mixture was stirred at room temperature overnight and then evaporated to remove THF. The mixture was dissolved in water and extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated. The crude product was purified by column chromatography (CH2Cl2:EtOAc=10:1) to get yellow solid product. MS: calc'd 594 (MH+), exp 594 (MH+).

Workup

  1. customevaporated
  2. customto remove THF
  3. dissolutionThe mixture was dissolved in water
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by column chromatography (CH2Cl2:EtOAc=10:1)
  10. customto get yellow solid product

Sources & evidence

ORD record
ord-b32e868c6d2b43aea803d8f3db5e32f9
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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