Propargyl bromide → (2-Azido-benzyl)-prop-2-ynyl-carbamic acid

HRID 1253896Notes

Reaction equation

HRID 1253896 reaction equation
[H-].[Na+].C([O:7][C:8](=[O:20])[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]=[N+:18]=[N-:19])(C)(C)C.[CH2:21](Br)[C:22]#[CH:23]>CCCCCC.CN(C=O)C>[N:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][N:9]([CH2:23][C:22]#[CH:21])[C:8](=[O:20])[OH:7])=[N+:18]=[N-:19]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 59176460Tert-butyl 2-azidobenzylcarbamate

Product 1

HCID 86648335(2-Azido-benzyl)-prop-2-ynyl-carbamic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Sodium hydride (5.0 mg, 0.120 mmol, 60% suspension in mineral oil) was washed with hexane (2 mL) in a flame dried round bottomed flask under nitrogen atmosphere. To the resulting free floating powder, was added a solution of (2-azido-benzyl)-carbamic acid tert-butyl ester (20 mg, 0.08 mmol) in dry DMF (1 mL) at 0° C. The reaction mixture was stirred at this temperature for 30 min. Propargyl bromide (0.021 mL, 0.24 mmol) was added and the reaction mixture was stirred at r.t. for 2 h. After the completion of reaction as confirmed by TLC, crude product was extracted with ethylacetate (10 mL). The organic layer was washed with water (2×5 mL). Organic layer was dried over Na2SO4 and concentrated in vacuo to afford the crude compound which was purified by column chromatography (silica gel; 1:9 EtOAc:Pet.Ether) to afford (2-azido-benzyl)-prop-2-ynyl-carbamic acid ten-butyl ester (20 mg, 87%) as a viscous oil.

Workup

  1. customdried round bottomed flask under nitrogen atmosphere
  2. stirringthe reaction mixture was stirred at r.t. for 2 h
  3. customAfter the completion of reaction
  4. extractionwas extracted with ethylacetate (10 mL)
  5. washThe organic layer was washed with water (2×5 mL)
  6. dry with materialOrganic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto afford the crude compound which
  9. customwas purified by column chromatography (silica gel; 1:9 EtOAc:Pet.Ether)

Sources & evidence

ORD record
ord-c91c159061954f2aabf241e0bcb1135c
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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