Azidotrimethylsilane → HCID 53648826, compound

HRID 1934382Notes

Reaction equation

HRID 1934382 reaction equation
[Si:1]([N:8]1[C@H:11]([C:12]#[CH:13])[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([N:19]=[N+:20]=[N-:21])(C)C>>[Si:1]([N:8]1[C@H:11]([C:12]2[CH:13]=[N:21][NH:20][N:19]=2)[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 18734916HCID 18734916, compound

Product 1

HCID 53648826HCID 53648826, compoundYield 8.3%

Conditions

Temperature
80 °C

Procedure

A mixture of 1-tert-butyldimethylsilyl-4(S)-ethynyl-2-azetidinone (3.0 g) and trimethylsilylazide (15 ml) was heated at 80° C. for 20 hours. The reaction mixture was allowed to room temperature and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with n-hexane ethyl acetate=(1:1) to give 1-tert-butyldimethylsilyl-4(S)-(2H-1,2,3-triazol-4-yl)-2-azetidinone (0.3 g, 8.3%) as a pale yellow solid.

Workup

  1. customwas allowed to room temperature
  2. customevaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with n-hexane ethyl acetate=(1:1)

Sources & evidence

ORD record
ord-d6d006d8cb90480d85c2cb05b6633a11
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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