Tributylstannane → HCID 53866326, compound

HRID 1701671Notes

Reaction equation

HRID 1701671 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15](Cl)[N:14]([C:17](=[C:34]([CH3:38])[CH2:35][O:36][CH3:37])[C:18]([O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C:13]1=[O:39])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(CC(NC1C(Cl)N(C(=C(C)C)C(OC(C2C=CC=CC=2)C2C=CC=CC=2)=O)C1=O)=O)C1C=CC=CC=1.C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:17](=[C:34]([CH3:38])[CH2:35][O:36][CH3:37])[C:18]([O:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[C:13]1=[O:39])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 20534636HCID 20534636, compoundHCID 86736893HCID 86736893, compound

Product 1

HCID 53866326HCID 53866326, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Benzhydryl 2-(3-phenoxyacetamido-4-chloro-2-oxoazetidin-1-yl)-3-methyl-4-methoxy-2-butenoate [prepared from benzhydryl 2-(3-phenoxyacetamido-4-chloro-2oxoazetidin-1-yl)-3-methyl-2-butenoate using the general procedures described in Examples 7 and 8(A) hereinabove] (264 mg, 0.5 mmol) was dissolved in 1 ml of toluene with 0.6 mmol of tri(butyl)tin hydride and 0.6 mmol of azobisisobutyronitrile (99 mg) and heated at 62° with stirring under a nitrogen atmosphere. The reaction solvent was removed under reduced pressure to provide an impure product which was purified by preparative thin layer chromatography. (1:2/ethyl acetate:hexane). Yield --54 mg of title product.

Workup

  1. temperatureheated at 62°
  2. customThe reaction solvent was removed under reduced pressure
  3. customto provide an impure product which
  4. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-ecade2371fa243ceb1578f345bf8059b
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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