Triethylamine → HCID 59418316, compound
Reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[C:13]([NH2:15])=[O:14].C(N(CC)CC)C.[Br:23][CH:24]([CH3:28])[C:25](Br)=[O:26]>CN(C=O)C>[Br:23][CH:24]([CH3:28])[C:25]([NH:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[C:13]([NH2:15])=[O:14])=[O:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of C2 (5.0 g, 23.8 mmol) and triethylamine (3.65 mL, 26.2 mmol) in anhydrous DMF (50 mL) was cooled in an ice bath and treated drop-wise with 2-bromopropanoyl bromide (5.4 g, 25 mmol). The mixture was stirred at 0° C. for 30 mins, warmed to room temperature and stirred at ambient temperature for an additional 2 h. The reaction was partitioned between EtOAc (200 mL) and aqueous 2N hydrochloric acid (500 mL); the organic phase was washed with saturated aqueous sodium bicarbonate solution (400 mL), saturated aqueous sodium chloride solution (200 mL) and dried over sodium sulfate. Filtration and concentration of the filtrate provided crude C24 as an orange residue, which was used in the next step without purification,
Workup
- temperaturewarmed to room temperature
- stirringstirred at ambient temperature for an additional 2 h
- customThe reaction was partitioned between EtOAc (200 mL) and aqueous 2N hydrochloric acid (500 mL)
- washthe organic phase was washed with saturated aqueous sodium bicarbonate solution (400 mL), saturated aqueous sodium chloride solution (200 mL)
- dry with materialdried over sodium sulfate
- filtrationFiltration and concentration of the filtrate
- customprovided crude C24 as an orange residue, which
- customwas used in the next step without purification
Sources & evidence
- ORD record
- ord-2e212b0589eb43cc8fcfff14e4f62105
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618117B2
Reaction notes
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