Benzyl succinimido carbonate → HCID 60134480, compound

HRID 2061070Notes

Reaction equation

HRID 2061070 reaction equation
[CH2:1]([N:3]([CH2:10][CH3:11])[CH2:4][CH2:5][C:6]([CH3:9])([NH2:8])[CH3:7])[CH3:2].[C:12](ON1C(=O)CCC1=O)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>C1COCC1>[CH2:10]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][C:6]([NH:8][C:12](=[O:13])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:9])[CH3:7])[CH3:11]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 64678504HCID 64678504, compound

Product 1

HCID 60134480HCID 60134480, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude N1,N1-diethyl-3-methylbutane-1,3-diamine (7.00 g, 44.2 mmol) was dissolved into THF (100 mL). To this solution was added CbzOSu (11.0 g, 1 equiv, 44.2 mmol) in one portion. The reaction was left to stir at room temperature for 2 d. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (150 mL) and water (100 mL). The layers were separated and the organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a pale yellow oil. The crude oil was purified on an ISCO purification system with gradient elution from 1-5% methanol in DCM. The desired fraction was collected and concentrated to give a colorless oil (6.7 g, yield: 37.8%). 1H NMR (CDCl3, 400 MHz): δ 1.00-1.04 (t, J=7.0, 6H),1.37 (s, 6H), 1.57-1.61 (t, J=6.2, 2H), 2.45-2.51 (q, J=7.0, 4H), 2.52-2.56 (t, J=6.0, 2 H), 5.04 (s, 2H), 7.27-7.36 (m, 5H), 7.57 (bs, 1H). LRMS (ESI+) for C17H28N2O2 (292.2); Found: 293 (MH+).

Workup

  1. waitThe reaction was left
  2. customThe solvent was removed
  3. additionthe residue was taken up in a mixture of ethyl acetate (150 mL) and water (100 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with saturated sodium bicarbonate (2×100 mL), water (100 mL) and brine (100 mL)
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a pale yellow oil
  9. customThe crude oil was purified on an ISCO purification system with gradient elution from 1-5% methanol in DCM
  10. customThe desired fraction was collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-af5e1b8264b24cc6bc2f542d54c4f70f
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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