Tributylstannane → HCID 86751735, compound

HRID 1940027Notes

Reaction equation

HRID 1940027 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:6][N:7]1[C:13](=[O:14])[C@@H:12]2[C@H:8]1[C@@H:9](OC(N1C=CN=C1)=S)[CH2:10][N:11]2[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH2:6][N:7]1[C:13](=[O:14])[C@@H:12]2[C@H:8]1[CH2:9][CH2:10][N:11]2[C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86751736HCID 86751736, compound

Product 1

HCID 86751735HCID 86751735, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

200 g (0.38 mol) of benzyl (1S,4S,5S)-6-(3,4-dimethoxybenzyl)-7-oxo-4-[[(1-imidazolyl)thiocarbonyl]oxy]-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate were heated to 80° C. in 4.2liters of toluene. A solution of 213 ml (0.8 mol) of tributyltin hydride and 6.9 g (0.04 mol) of AIBN in 320 ml of toluene were added dropwise thereto while stirring. After completion of the dropwise addition the mixture was stirred at this temperature for a further 45 minutes before the solvent was removed under reduced pressure. There remained behind a yellowish turbid oil which was chromatographed over 1100 g of silica gel (0.063-0.2 mm particle size with 1) ethyl acetate: hexane 1:10; 2) ethyl acetate: hexane 2:1.

Workup

  1. additionAfter completion of the dropwise addition the mixture
  2. stirringwas stirred at this temperature for a further 45 minutes before the solvent
  3. customwas removed under reduced pressure
  4. customwas chromatographed over 1100 g of silica gel (0.063-0.2 mm particle size with 1) ethyl acetate: hexane 1:10

Sources & evidence

ORD record
ord-8170cf044cd04fdebe87e5aa2d8a0dca
Source dataset
uspto-grants-1997_12
Patent number
US05698577

Reaction notes

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