1,1'-(Diazomethylene)bis(benzene) → HCID 88784431, compound

HRID 2398133Notes

Reaction equation

HRID 2398133 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([OH:21])=[O:20])=[C:8]([CH2:11][S:12][C:13]3[S:14][C:15]([CH3:18])=[N:16][N:17]=3)[CH2:9][S:10][C@H:5]12)=[O:2].[C:24]1([C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N+]=[N-])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1.C(O)(=O)C>[CH:1]([NH:3][C@@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([O:21][CH:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:20])=[C:8]([CH2:11][S:12][C:13]3[S:14][C:15]([CH3:18])=[N:16][N:17]=3)[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

5

Reactant 2

HCID 612301,1'-(Diazomethylene)bis(benzene)HCID 88783875HCID 88783875, compound

Product 1

HCID 88784431HCID 88784431, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7β-formamido-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylic acid (8.5 g) in tetrahydrofuran (300 ml) was treated with an excess of a solution of diphenyldiazomethane in petroleum (300 ml) and the mixture was kept at 20° for 16 hours. A few drops of acetic acid were added and solvents were removed under reduced pressure. The resulting yellow syrup was dissolved in ethyl acetate and washed with sodium bicarbonate solution. A solid (7.5 g) precipitated and was dried in vacuo. A sample (5.77g) of the wet solid was dissolved in methylene chloride, and the solution was dried and concentrated under reduced pressure. The residue was crystallised from methanol to give the title ester (5.08 g),m.p. 108° (decomp.), λmax. (EtOH) 268nm (ε 12,400), τ (CDCl3 + a little DMSO-d6) values include 1.50 (d, J 9 Hz; NH), 1.72 (s; HCO), 6.30 (singlet; C-2 CH2) and 7.31 (singlet;CH3).

Workup

  1. customsolvents were removed under reduced pressure
  2. dissolutionThe resulting yellow syrup was dissolved in ethyl acetate
  3. washwashed with sodium bicarbonate solution
  4. customA solid (7.5 g) precipitated
  5. customwas dried in vacuo
  6. dissolutionA sample (5.77g) of the wet solid was dissolved in methylene chloride
  7. customthe solution was dried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was crystallised from methanol

Sources & evidence

ORD record
ord-b92ba94687164f0fbd57a97b454da32a
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

Loading…