Tetrabutylammonium Fluoride → HCID 68814249, compound

HRID 730588Notes

Reaction equation

HRID 730588 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([C:17]3[CH:21]=[CH:20][N:19]([Si](C(C)C)(C(C)C)C(C)C)[CH:18]=3)=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:9]1=[O:39])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>O1CCOCC1.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:12]2[C:13]([C:17]3[CH:21]=[CH:20][NH:19][CH:18]=3)=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:9]1=[O:39])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 22728543Water ethylacetateHCID 68814838HCID 68814838, compound

Product 1

HCID 68814249HCID 68814249, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-benzyl-2-oxo-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester (0.768 g, 1.40 mmol) in 30 ml 1,4-dioxane was added tetrabutylammonium fluoride (1.548 mL of a 1M solution in tetrahydrofuran, 1.548 mmol) dropwise over 5 minutes. The reaction mixture was stirred for 45 minutes, and was then added to 200 mL of 1:1 water/ethyl acetate. The layers were separated and the aqueous layer was extracted twice with 100 mL ethyl acetate. The combined organic fractions were dried over sodium sulfate and concentrated in vacuo and purified by flash chromatography (20 to 40% gradient ethyl acetate in hexanes) to give 0.447 g of crude 3-benzyl-2-oxo-7-(1H-pyrrol-3-yl)-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester. This material was dissolved in 7 mL tetrahydrofuran and cooled to 0° C. under nitrogen. To this solution was added di-tert-butyldicarbonate (0.752 g, 3.45 mmol) and 4-dimethylaminopyridine (14 mg, 0.115 mmol) and stirring was continued for one hour as the reaction mixture was allowed to warm to room temperature. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography (1 to 10% gradient ethyl acetate in hexanes) to give 0.550 g of 3-benzyl-7-(1-tert-butoxycarbonyl-1H-pyrrol-3-yl)-2-oxo-2,3-dihydro-benzoimidazole-1-carboxylic acid tert-butyl ester, MS: 490 (M+H)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with 100 mL ethyl acetate
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (20 to 40% gradient ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6537ee838a1e48f9a5b1b5700402f08d
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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