Ammonium Acetate → HCID 53701042, compound

HRID 1358484Notes

Reaction equation

HRID 1358484 reaction equation
[Si]([O:8][CH2:9][C@H:10]([N:22]1[CH:26]=[C:25]([C:27]([NH2:29])=[O:28])[N:24]=[CH:23]1)[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C([O-])(C)=O.[NH4+]>C1COCC1>[OH:8][CH2:9][C@H:10]([N:22]1[CH:26]=[C:25]([C:27]([NH2:29])=[O:28])[N:24]=[CH:23]1)[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 2724141Tetrabutylammonium FluorideHCID 53879351HCID 53879351, compound

Product 1

HCID 53701042HCID 53701042, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cooled solution of 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(1-indolyl)-2-butyl]imidazole-4-carboxamide (176.3 mg, 0.427 mmol) in THF (5 ml) was added dropwise 1.0 M Bu4NF in THF (641 ml). After the addition was completed, the reaction mixture was stirred at ice-bath temperature for 30 minutes. 25% AcONH4 (4 ml) was added, and the resulting mixture was stirred for several minutes and then extracted with ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate) and concentrated in vacuo. The residue was purified by silica gel (6 g) column chromatography eluting with chloroform/methanol. (10:1) to give 1-[(R)-1-hydroxy-4-(1-indolyl)-2-butyl]imidazole-4-carboxamide (81.7 mg, 64.1%) as a white solid.

Workup

  1. additionAfter the addition
  2. stirringthe resulting mixture was stirred for several minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel (6 g) column chromatography
  8. washeluting with chloroform/methanol

Sources & evidence

ORD record
ord-3a5f9d3589cd4ef193f686661d09fff0
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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