Potassium Carbonate → 7-(2-{[2-(4-Cyanophenoxy)ethyl]methanesulfonylamino}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 899147Notes

Reaction equation

HRID 899147 reaction equation
Br[CH2:2][CH2:3][N:4]([CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)[S:5]([CH3:8])(=[O:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[C:26]([O:30][C:31]([N:33]1[CH2:40][CH:39]2[O:41][CH:35]([CH2:36][NH:37][CH2:38]2)[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>C(#N)C>[C:26]([O:30][C:31]([N:33]1[CH2:34][CH:35]2[O:41][CH:39]([CH2:38][N:37]([CH2:2][CH2:3][N:4]([CH2:9][CH2:10][O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=3)[S:5]([CH3:8])(=[O:7])=[O:6])[CH2:36]2)[CH2:40]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 69075823N-(2-Bromoethyl)-N-[2-(4-cyanophenoxy)ethyl]methanesulfonamide

Product 1

HCID 690747607-(2-{[2-(4-Cyanophenoxy)ethyl]methanesulfonylamino}ethyl)-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of N-(2-bromoethyl)-N-[2-(4-cyanophenoxy)ethyl]methane-sulfonamide (6 g, 0.019 mol; see Preparation C above) and anhydrous potassium carbonate (3.6 g, 0.026 mol) in dry acetonitrile (100 mL) was added 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (4.35 g, 0.019 mol; see WO 01/28992), and the resultant mixture was then stirred at 50-55° C. overnight. After completion of the reaction (as determined by TLC), the mixture was filtered and concentrated. The crude product was further purified by column chromatography (silica gel: 60-120 mesh, eluent: chloroform-methanol, 99:1). Yield: 4.2 g (46%).

Workup

  1. customAfter completion of the reaction (as determined by TLC)
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated
  4. customThe crude product was further purified by column chromatography (silica gel: 60-120 mesh, eluent: chloroform-methanol, 99:1)

Sources & evidence

ORD record
ord-a11bcff4278344f384a6615848989c30
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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