Triethylamine → HCID 59296770, compound
Reaction equation
[C:1]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:21]=[C:19]([OH:20])[C:17]([OH:18])=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:22](=O)(ON1C(=O)CCC1=O)[O:23]N1C(=O)CCC1=O.C(N(CC)CC)C>ClCCl>[C:4]([O:3][C:1]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[O:18][C:22](=[O:23])[O:20][C:19]=2[CH:21]=1)[C:10]([OH:12])=[O:11])=[O:2])([CH3:6])([CH3:7])[CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Boc-L-DOPA (22.3 g, 75 mmol) and disuccinimidyl carbonate (DSC, 80% pure, 24 g, 75 mmol) were suspended in anhydrous dichloromethane (500 mL) and triethylamine (21 mL, 150 mmol) was added dropwise at 0° C. The resulting reaction mixture was stirred at 0° C. for 30 min. The suspension became a clear solution. HPLC indicated a completed reaction. The reaction mixture was washed with 10% citric acid (200 mL) and water (200 mL×5) to remove triethylamine and N-hydroxysuccinamide. The organic layer was collected, dried over MgSO4, and concentrated to provide the title compound (16) (22 g, 91% yield), 1H NMR (400 MHz, CDCl3): δ 1.43 (s, 9H), 3.11 (dd, 1H, J=14, 6.8 Hz), 3.27 (dd, 1H, J=14, 6.8 Hz), 4.59 (dd, 1H, J=14, 6.8 Hz), 5.03 (d, 1H, NH, J=8.0 Hz), 7.05 (dd, 1H, J=8, 2 Hz), 7.11 (d, 1H, J=2 Hz), 7.18 (d, 1H, J=8 Hz). MS (ESI) m/z 321.9 (M−H)−.
Workup
- customThe resulting reaction mixture
- customa completed reaction
- washThe reaction mixture was washed with 10% citric acid (200 mL) and water (200 mL×5)
- customto remove triethylamine and N-hydroxysuccinamide
- customThe organic layer was collected
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c40acd9d7eee428683aaafd706968769
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324272B2
Reaction notes
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