1,1'-(Diazomethylene)bis(benzene) → HCID 131720181, compound

HRID 1376855Notes

Reaction equation

HRID 1376855 reaction equation
[C:1]1([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:26][CH2:27][CH:28]2[N:31]([CH2:32][C:33]([OH:35])=[O:34])[C:30](=[O:36])[CH:29]2[NH:37][C:38]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CCOCC.O1CCOCC1>[CH3:16][C:17]1[CH:18]=[CH:19][C:20]([S:23]([O:26][CH2:27][C@H:28]2[N:31]([CH2:32][C:33]([O:35][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:34])[C:30](=[O:36])[C@H:29]2[NH:37][C:38]([C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)(=[O:25])=[O:24])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)2×HCID 22916786HCID 22916786, compound

Product 1

HCID 131720181HCID 131720181, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2.68 g of diphenyldiazomethane in 59 ml of ether was added to a solution of 6.55 g of 4-{[(4-methylphenyl)-sulfonyloxy]-methyl}-3-(triphenylmethylamino)-2-oxo-azetidin-1-yl-acetic acid in 70 ml of dioxane and after stirring for 3 hours at 20° C. 448 mg of diphenyldiazomethane were added. The mixture was stirred at 20° C. for 16 hours and was then evaporated to dryness under reduced pressure. The residue was chromatographed over silica and was eluted with a 10-0.5 methylene chloride-ether mixture to obtain 7.5 g of diphenylmethyl racemic cis 4-{[(4-methylphenyl)-sulfonyloxy]-methyl)-3-triphenylmethylamino-2-oxo-azetidin-1-yl-acetate.

Workup

  1. stirringThe mixture was stirred at 20° C. for 16 hours
  2. customwas then evaporated to dryness under reduced pressure
  3. customThe residue was chromatographed over silica
  4. washwas eluted with a 10-0.5 methylene chloride-ether mixture

Sources & evidence

ORD record
ord-8819dc927e2e4deca9477ddda373908e
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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