Benzyl succinimido carbonate → HCID 60134461, compound

HRID 2061048Notes

Reaction equation

HRID 2061048 reaction equation
[CH2:1]([N:5]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:6][CH2:7][C:8]([CH3:11])([NH2:10])[CH3:9])[CH2:2][CH2:3][CH3:4].[C:16](ON1C(=O)CCC1=O)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1>[CH2:1]([N:5]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:6][CH2:7][C:8]([NH:10][C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:11])[CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 60134562HCID 60134562, compound

Product 1

HCID 60134461HCID 60134461, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude N1,N1-dibutyl-3-methylbutane-1,3-diamine (10.18 g, 47.4 mmol) was dissolved into THF (237 mL, 0.2 M). To this solution was added CbzOSu (11.8 g, 1 equiv, 47.4 mmol) in one portion. The reaction was left to stir at room temperature for 17 h. The solvent was removed and the residue was taken up in a mixture of ethyl acetate (600 mL) and water (200 mL). The layers were separated and the organic layer washed with water (2×300 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 60-80% ethyl acetate in hexanes. The desired fractions were collected and concentrated to give a colorless oil (12.6 g, 76.3%). LRMS (ESI+) for C21H36N2O2 (348.3); Found: 349 (MH+).

Workup

  1. waitThe reaction was left
  2. customThe solvent was removed
  3. additionthe residue was taken up in a mixture of ethyl acetate (600 mL) and water (200 mL)
  4. customThe layers were separated
  5. washthe organic layer washed with water (2×300 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 60-80% ethyl acetate in hexanes
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-f104c3c244fc43c98aee7a5faba78ce8
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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