Azidotrimethylsilane → HCID 118379772, compound

HRID 708528Notes

Reaction equation

HRID 708528 reaction equation
[CH3:1][C@H:2]([N:5]([CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]#[CH:4].[N:24]([Si](C)(C)C)=[N+:25]=[N-:26]>CN(C=O)C.CO.[Cu]I>[N:24]1[NH:25][N:26]=[C:3]([C@@H:2]([N:5]([CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:10])[CH3:11])[CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 118379712HCID 118379712, compound

Product 1

HCID 118379772HCID 118379772, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (S)-tert-butyl but-3-yn-2-yl(3-((tert-butoxycarbonyl)amino)propyl)carbamate (710 mg, 2.18 mmol), azidotrimethylsilane (452 μl, 3.26 mmol) and copper (I) iodide (21 mg, 0.11 mmol) in DMF/MeOH (1:1, 3.4 mL) was heated to 100° C. for 8 h. Upon cooling, the mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo and purified via silica gel chromatography (EtOAc-Heptane, 30-80%) to afford the title compound (636 mg, 79%) as an oil. LCMS: Rt=0.78 min, m/z=370.1 (M+1) Method 2m_acidic.

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture was filtered through a celite pad
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified via silica gel chromatography (EtOAc-Heptane, 30-80%)

Sources & evidence

ORD record
ord-4b2936e374fe4ca3a323efd56208b5c0
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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