Acetic Acid → HCID 15980223, compound

HRID 2078441Notes

Reaction equation

HRID 2078441 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12](=[O:25])[NH:13][CH2:14][CH2:15][N:16]1[CH2:23][CH:22]2[O:24][CH:18]([CH2:19][NH:20][CH2:21]2)[CH2:17]1)([CH3:10])([CH3:9])[CH3:8].Br[CH2:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=1.C(O)(=O)C.C(O)=O>C(#N)C>[C:32]([C:31]1[CH:34]=[CH:35][C:28]([CH2:27][N:20]2[CH2:19][CH:18]3[O:24][CH:22]([CH2:23][N:16]([CH2:15][CH2:14][NH:13][C:12](=[O:25])[O:11][C:7]([CH3:10])([CH3:8])[CH3:9])[CH2:17]3)[CH2:21]2)=[CH:29][CH:30]=1)#[N:33]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 284Formic AcidHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 9970422Tert-butyl[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamate

Product 1

HCID 15980223HCID 15980223, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (3.82 g, 27.6 mmol) was added to a mixture of tert-butyl[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]carbamate (5.00 g, 18.4 mmol; see WO 02/83690 and WO 2004/035592) and 4-(bromomethyl)benzonitrile (3.61 g, 18.4 mmol) in acetonitrile (150 mL). The mixture was heated to reflux overnight, cooled to room temperature, filtered and then evaporated. The residue was dissolved in dichloromethane (100 mL), washed with water and dried over MgSO4. Purification by preparative HPLC gave 7.04 g (78%) of the title compound as a salt with one equivalent of acetic acid and one equivalent of formic acid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-c8aa5a09b45c40469ec8f6618e6a3173
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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