Potassium Carbonate → HCID 178451398, compound

HRID 733422Notes

Reaction equation

HRID 733422 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([CH:16]1[C:29]3[CH:28]=[CH:27][C:26]([C:30]#[N:31])=[CH:25][C:24]=3[O:23][C:22]3[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.NO.C(=O)([O-])[O-].[K+].[K+].Cl.[OH-:42].[NH4+:43]>C(O)C.O>[C:1]([O:5][C:6]([N:8]1[CH:9]2[CH2:15][CH2:14][CH:13]1[CH2:12][CH:11]([CH:16]1[C:29]3[CH:28]=[CH:27][C:26]([C:30](=[NH:43])[NH:31][OH:42])=[CH:25][C:24]=3[O:23][C:22]3[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:10]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 443297Hydroxyamine hydrochlorideHCID 13908798HCID 13908798, compoundHCID 578392203-(3-cyano-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Product 1

HCID 178451398HCID 178451398, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(3-cyano-9H-xanthen-9-yl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (635 mg; 0.877 mmol) in ethanol (10 mL) was added hydroxylamine hydrochloride (183 mg; 2.62 mmol) and potassium carbonate (242 mg; 1.75 mmol), and the mixture was heated to reflux for 16 h. More ammonium hydroxide hydrochloride (183 mg; 2.62 mmol) and potassium carbonate (242 mg; 1.75 mmol) were added, and the mixture was heated to reflux for 24 h. The mixture was allowed to cool to rt, water was added, and the solid was collected by filtration, yielding 402 mg (quant.) of 3-[3-(N-hydroxycarbamimidoyl)-9H-xanthen-9-yl]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester, 1n. The crude material was used as such in the next reaction.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 h
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 24 h
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-46291a43213e42a3af44200c1a6b9079
Source dataset
uspto-grants-2009_09
Patent number
US07589104B2

Reaction notes

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