Propargyl bromide → HCID 21250534, compound

HRID 576637Notes

Reaction equation

HRID 576637 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

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Product 1

HCID 21250534HCID 21250534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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

  1. customwas prepared under argon
  2. stirringthe reaction stirred at 0° C. for 15 min
  3. temperaturethen warmed to room temperature
  4. stirringstirred for additional 17 hr
  5. customThe reaction mixture was quenched with water
  6. extractionextracted two times with EtOAc
  7. washThe combined organic layers were washed with water (3×) and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product was carried to the next reaction without purification

Sources & evidence

ORD record
ord-7c3f83fbe8a54a9782ca69b940a7086b
Source dataset
uspto-grants-2015_05
Patent number
US09040504B2

Reaction notes

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