Tributylstannane → HCID 70518003, compound

HRID 851388Notes

Reaction equation

HRID 851388 reaction equation
[N+]([C@H:3]1[C:6](=[O:7])[NH:5][C@@H:4]1[CH2:8][C:9]([O:15][CH3:16])=[CH:10][C:11]([O:13][CH3:14])=[O:12])#[C-].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[CH3:16][O:15][C:9]([CH2:8][C@@H:4]1[CH2:3][C:6](=[O:7])[NH:5]1)=[CH:10][C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 86738872HCID 86738872, compound

Product 1

HCID 70518003HCID 70518003, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of methyl 4-[(2R,3R)-3-isocyano-4-oxoazetidin-2-yl]-3-methoxybut-2-enoate [(E,Z)-isomeric mixture](50 mg), tri-n-butyltin hydride (90 μl), and 2,2'-azobis-(2-methylpropionitrile) (5 mg) in benzene (5 ml) was heated to reflux for one hour under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and chromatographed on silica gel (2.5 g) eluting first with dichloromethane and then 4% methanol in dichloromethane to give methyl 3-methoxy-4-[(2R)-4-oxoazetidin-2-yl]but-2-enoate [(E,Z)-isomeric mixture](35 mg) as a crystalline solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for one hour under a nitrogen atmosphere
  3. customchromatographed on silica gel (2.5 g)
  4. washeluting first with dichloromethane

Sources & evidence

ORD record
ord-25a0cb1ad8b440678c2fc02b11987d0a
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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