Acetic Acid → N-(tert-Butyl)-1H-pyrrole-3-sulfonamide

HRID 1707929

Reaction equation

HRID 1707929 reaction equation
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C(O)(=O)C>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][NH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11078149TBAF tetrahydrofuranHCID 18960403N-(1,1-Dimethylethyl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole-3-sulfonamide

Product 1

HCID 19693846N-(tert-Butyl)-1H-pyrrole-3-sulfonamideYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(1,1-dimethylethyl)-1-[tris(1-methylethyl)sily]-1H-pyrrole-3-sulfonamide (1.7 g, 4.7 mmol) in 25 mL THF was treated with 5.2 mL of 1M tetrabutylammonium fluoride/THF solution, followed by 0.3 mL of acetic acid. After stirring 30 minutes at room temperature, the reaction mixture was filtered through silica with THF rinse, and the filtrate stripped. The solid residue was triturated with hexanes to afford 0.77 g of tan solids, m.p. 145°-147° C. dec.

Workup

  1. filtrationthe reaction mixture was filtered through silica with THF
  2. washrinse
  3. customThe solid residue was triturated with hexanes

Sources & evidence

ORD record
ord-5d832ec7db804cc5a611aa6687b957c7
Source dataset
uspto-grants-1994_10
Patent number
US05356862

Linked notes

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