Propargyl bromide → tert-Butyl 16-oxo-15-prop-2-yn-1-yl-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

HRID 1615839Notes

Reaction equation

HRID 1615839 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:9]2([CH2:13][CH2:12][CH2:11][CH2:10]2)[N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7][C:6]2([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[NH:5]1.[CH2:27](Br)[C:28]#[CH:29]>CN(C=O)C>[O:3]=[C:4]1[C:9]2([CH2:10][CH2:11][CH2:12][CH2:13]2)[N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:7][C:6]2([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[N:5]1[CH2:29][C:28]#[CH:27]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 66865409tert-Butyl 16-oxo-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

Product 1

HCID 58118691tert-Butyl 16-oxo-15-prop-2-yn-1-yl-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (23 mg, 0.575 mmol, 60% dispersion in mineral oil) was added to a stirred solution of tert-butyl 16-oxo-6,15-diazadispiro[4.2.6.2]hexadecane-6-carboxylate from Step A (92 mg, 0.273 mmol) in DMF (1 mL). When the gas evolution had ceased, propargyl bromide (70 mg, 0.471 mmol, 80 wt % in toluene) was added to the solution at ambient temperature. After 1 h, the reaction was quenched with water (30 mL) and extracted with EtOAc (30 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield the title compound. MS: m/z=397 (M+Na).

Workup

  1. customthe reaction was quenched with water (30 mL)
  2. extractionextracted with EtOAc (30 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0229014b12e74b89b654da22224eb77d
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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