Benzyl succinimido carbonate → HCID 60134423, compound

HRID 2061085Notes

Reaction equation

HRID 2061085 reaction equation
[CH2:1]([N:5]([CH3:12])[CH2:6][CH2:7][C:8]([CH3:11])([NH2:10])[CH3:9])[CH2:2][CH2:3][CH3:4].[C:13](ON1C(=O)CCC1=O)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>C1COCC1>[CH2:1]([N:5]([CH3:12])[CH2:6][CH2:7][C:8]([NH:10][C:13](=[O:14])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:11])[CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 60134523HCID 60134523, compound

Product 1

HCID 60134423HCID 60134423, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude N1-butyl-N1,3-dimethylbutane-1,3-diamine (5.00 g, 29.0 mmol) was dissolved into THF (100 mL). To this solution was added CbzOSu (7.23 g, 1 equiv, 29.0 mmol) in one portion. The reaction was left to stir at room temperature for 3 d. The solvent was removed and the residue was taken up in a mixture of diethyl ether (150 mL) and water (50 mL). The layers were separated and the organic layer washed with 1 M sodium carbonate (2×50 mL), 1M HCl (50 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 10-80% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a white solid (3.55 g, yield: 40.0%). 1H NMR (CDCl3, 400 MHz): δ 0.83-0.87 (t, J=7.2, 3H), 1.25-1.35 (m, 2H), 1.40 (s, 6H), 1.41-1.45 (m, 2H), 1.59-1.62 (t, J=6.4, 2H), 2.18 (s, 3H), 2.28-2.32 (t, J=6.4, 2H), 2.43-2.47 (t, J=6.4, 2H), 5.04 (s, 2H), 7.27-7.37 (m, 5H). LRMS (ESI+) for C18H30N2O2 (306.2); Found: 307 (MH+).

Workup

  1. waitThe reaction was left
  2. customThe solvent was removed
  3. additionthe residue was taken up in a mixture of diethyl ether (150 mL) and water (50 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with 1 M sodium carbonate (2×50 mL), 1M HCl (50 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 10-80% ethyl acetate in hexanes
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e95483adc3c347f0ba58d6ce2a92e97c
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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