Propargyl bromide → HCID 21250534, compound
Reaction equation
[C:1]([NH:8][CH2:9][C:10]#[CH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:14](Br)[C:15]#[CH:16]>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[N:8]([CH2:16][C:15]#[CH:14])[CH2:9][C:10]#[CH:11])([CH3:5])([CH3:6])[CH3:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of N-Boc-propargylamine (2.63 g, 16.9 mmol) and DMF (35 mL) was prepared under argon and cooled to 0° C. for 20 min. Sodium hydride (60%, 0.714 g, 17.9 mmol) was added and the reaction stirred at 0° C. for 30 min. Propargyl bromide (80% in toluene, 2.7 mL, 24.2 mmol) in DMF (5 mL) was added slowly and the reaction stirred at 0° C. for 15 min then warmed to room temperature and stirred for additional 17 hr. The reaction mixture was quenched with water and extracted two times with EtOAc. The combined organic layers were washed with water (3×) and brine, dried over Na2SO4, filtered, and concentrated. The crude product was carried to the next reaction without purification. ESI-MS m/z 194 (MH)+.
Workup
- customwas prepared under argon
- stirringthe reaction stirred at 0° C. for 15 min
- temperaturethen warmed to room temperature
- stirringstirred for additional 17 hr
- customThe reaction mixture was quenched with water
- extractionextracted two times with EtOAc
- washThe combined organic layers were washed with water (3×) and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was carried to the next reaction without purification
Sources & evidence
- ORD record
- ord-94d93455a37f4b2eb7c649cc2a8ab074
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376454B2
Reaction notes
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