Azidotrimethylsilane → HCID 131733857, compound

HRID 708550Notes

Reaction equation

HRID 708550 reaction equation
[CH2:1]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:2][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]#[CH:5].[N:22]([Si](C)(C)C)=[N+:23]=[N-:24]>CN(C=O)C.CO.[Cu](I)I>[N:22]1[NH:23][N:24]=[C:4]([C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2][CH2:1][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=1

Participants

5

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 118379991HCID 118379991, compound

Product 1

HCID 131733857HCID 131733857, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-di-tert-butyl pent-4-yne-1,3-diyldicarbamate in DMF/MeOH (3.7 mL, 1.2:1) was added azidotrimethylsilane (330 μL, 2.38 mmol) and copper iodide (15 mg, 0.079 mmol). The mixture was heated at 100° C. for 16 h, cooled to rt then filtered through celite. The filtrate was concentrated in vacuo and the crude residue was purified via silica gel chromatography (EtOAc-Heptane) to afford the title compound. LCMS: Rt=0.68 min, m/z=342.1 (M+1) Method 2m_acidic.

Workup

  1. temperaturecooled to rt
  2. filtrationthen filtered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe crude residue was purified via silica gel chromatography (EtOAc-Heptane)

Sources & evidence

ORD record
ord-9d08dca8e9b744fa93ccbcf572dbb067
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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