Tributylstannane → HCID 70993762, compound

HRID 451316Notes

Reaction equation

HRID 451316 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[O:13]=[C:14]1[N:20]2[CH2:21][C@@H:16]([CH2:17][CH2:18][C@H:19]2[C:22]([NH:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[O:23])[N:15]1OC(OC1C=CC=CC=1)=S.C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1>[O:13]=[C:14]1[N:20]2[CH2:21][C@@H:16]([CH2:17][CH2:18][C@H:19]2[C:22]([NH:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[O:23])[NH:15]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86659594HCID 86659594, compound

Product 1

HCID 70993762HCID 70993762, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

AIBN (0.1 eq.) is added to a solution of tert-butyl 4-[({(2S,5R)-7-oxo-6-[(phenoxycarbonothioyl)oxy]-1,6-diazabicyclo[3.2.1]oct-2-yl}carbonyl)amino]piperidine-1-carboxylate in dry benzene and the resulting mixture is heated to reflux. A solution of tributyltin hydride (1.25 eq.) in benzene is added over a period of one hour and the resulting mixture is refluxed for an additional 3 hours. The reaction mixture is concentrated under vacuum and the residue is purified by silica gel chromatography to afford the title compound.

Workup

  1. temperaturethe resulting mixture is heated to reflux
  2. temperaturethe resulting mixture is refluxed for an additional 3 hours
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. customthe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-3b925d7101344e52853d972ec522ba28
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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