Benzyl azide → HCID 68989761, compound

HRID 240768Notes

Reaction equation

HRID 240768 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].C(N([Sn:14]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18])C(=O)OC)C.[CH2:27]([N:34]=[N+:35]=[N-:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:27]([N:34]1[C:2]([C:1]([O:5][CH3:6])=[O:4])=[C:3]([Sn:14]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH2:25][CH3:26])[N:36]=[N:35]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 12152Benzyl azideHCID 13536Methyl propiolateHCID 3384006Methyl ethyl(tributylstannyl)carbamate

Product 1

HCID 68989761HCID 68989761, compound

Conditions

Temperature
70 °C

Procedure

Methyl propiolate (5.75 g, 68.4 mmol) was added to methyl ethyl(tributylstannyl)carbamate (26.9 g, 68.6 mmol) in a large sealed tube. The mixture was heated to 70° C. overnight. The mixture was cooled to ambient temperature and the vial was stirred unsealed for 10 minutes. Benzyl azide (10.2 mL, 81.6 mmol) was added, and the vial was resealed and heated to 130° C. overnight. The mixture was purified by silica gel chromatography eluting with a gradient of 5-40% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 508.3 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperatureheated to 130° C. overnight
  3. customThe mixture was purified by silica gel chromatography
  4. washeluting with a gradient of 5-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c2f77ffc97164a61b09fda842be0ba35
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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