TBAF tetrahydrofuran → HCID 178460741, compound

HRID 621818Notes

Reaction equation

HRID 621818 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[CH:24]([S:27][C:28]1[CH:32]=[C:31]([Si](C)(C)C)[O:30][C:29]=1[C:37]([NH:39][C:40]1[NH:44][N:43]=[N:42][N:41]=1)=[O:38])([CH3:26])[CH3:25]>O1CCCC1>[CH:24]([S:27][C:28]1[CH:32]=[CH:31][O:30][C:29]=1[C:37]([NH:39][C:40]1[NH:44][N:43]=[N:42][N:41]=1)=[O:38])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 178460744HCID 178460744, compound

Product 1

HCID 178460741HCID 178460741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.0 mL (5.0 mmol, 1.1 equiv) of 1.0 M tetra-n-butylammonium fluoride/tetrahydrofuran is added to a room temperature solution of 1.51 g (4.64 mmol) of 3-isopropylthio-5-trimethylsilyl-N-1H-tetrazol-5-yl-2-furancarboxamide in 15 mL of tetrahydrofuran. The resulting mixture is stirred at room temperature for 18 hours and concentrated in vacuo. The residue is suspended in water (100 mL) and acidified with 10% aqueous hydrochloric acid. The precipitate is isolated by vacuum filtration and recrystallized from toluene affording 1.26 g (1.77 g theo., 71%) of the carbamoyltetrazole as a tan solid; mp 201°-203° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe precipitate is isolated by vacuum filtration
  3. customrecrystallized from toluene affording 1.26 g (1.77 g theo., 71%) of the carbamoyltetrazole as a tan solid

Sources & evidence

ORD record
ord-cefcf6460604454299061c76c8f4e5b9
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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