Benzyl succinimido carbonate → HCID 60134582, compound

HRID 2061075Notes

Reaction equation

HRID 2061075 reaction equation
[N:1]1([CH2:8][CH2:9][C:10]([CH3:13])([NH2:12])[CH3:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:14](ON1C(=O)CCC1=O)([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>C(Cl)Cl>[N:1]1([CH2:8][CH2:9][C:10]([NH:12][C:14](=[O:15])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:13])[CH3:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 646783261226913-97-8

Product 1

HCID 60134582HCID 60134582, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 4-(Azepan-1-yl)-2-methylbutan-2-amine (4.54 g, 24.6 mmol) was dissolved into DCM (120 mL). To this solution was added CbzOSu (6.13 g, 1 equiv, 24.6 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 (8.33 g). 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 (3.69 g, yield: 47.1%). LRMS (ESI+) for C19H30N2O2 (318.2); Found: 319 (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 (8.33 g)
  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-304c763083cd4a038f2d104e08f04d94
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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