Tetrahydrofuran → HCID 60134491, compound

HRID 2061088Notes

Reaction equation

HRID 2061088 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][CH2:5][N:6]([CH3:13])[CH2:7][CH2:8][C:9]([CH3:12])([NH2:11])[CH3:10].C1COCC1.C(=O)([O-])O.[Na+].[C:25](ON1C(=O)CCC1=O)([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>O>[CH3:14][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][N:6]([CH3:13])[CH2:7][CH2:8][C:9]([NH:11][C:25](=[O:26])[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([CH3:10])[CH3:12]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 64681435HCID 64681435, compound

Product 1

HCID 60134491HCID 60134491, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Crude N1-(3-(Dimethylamino)propyl)-N1,3-dimethylbutane-1,3-diamine (18.0 g, 31.9 mmol) was dissolved into THF (200 mL). Sodium hydrogen carbonate (14.0 g, 0.167 mol) dissolved in water (200 mL) was added to reaction to give a solution. CbzOSu (7.95 g, 1 equiv, 31.9 mmol) was added in one portion to the reaction and left to stir at room temperature for 16 h. The organic solvent was removed via rotovap and the aqueous concentrated to ˜100 mL. The aqueous was extracted with DCM (2×200 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil. The crude oil was purified on a Shimadzu Prep-LC utilizing water/acetonitrile and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. The desired fractions were collected and lyophilized to give a colorless oil (5.57 g, yield: 52.1%). LRMS (ESI+) for C19H33N3O2 (335.3); Found: 336 (MH+).

Workup

  1. additionwas added to reaction
  2. customto give a solution
  3. waitleft
  4. customThe organic solvent was removed via rotovap
  5. concentrationthe aqueous concentrated to ˜100 mL
  6. extractionThe aqueous was extracted with DCM (2×200 mL)
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to a pale yellow oil
  10. customThe crude oil was purified on a Shimadzu Prep-LC
  11. customFractions were collected
  12. customThe desired fractions were collected

Sources & evidence

ORD record
ord-acbbb4976b984624b427363dcabaa047
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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