Acetic Acid → HCID 15980223, compound

HRID 1992393Notes

Reaction equation

HRID 1992393 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]12[O:15][CH:11]([CH2:12][NH:13][CH2:14]1)[CH2:10][N:9]([CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:8]2.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:21]([O:20][C:19](=[O:25])[NH:18][CH2:17][CH2:16][N:9]1[CH2:10][CH:11]2[O:15][CH:7]([CH2:14][N:13]([CH2:27][C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=3)[CH2:12]2)[CH2:8]1)([CH3:22])([CH3:24])[CH3:23]

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) and 4-(bromomethyl)benzonitrile (3.61 g, 18.4 mmol) in acetonitrile (150 mL). The mixture was heated to reflux over night, cooled to room temperature, filtered and 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 sub.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 over night
  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-c9383cb43deb4c9798e7d7269a5e020e
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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