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

HRID 1707182Notes

Reaction equation

HRID 1707182 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 (5.77 g) 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) 268 nm (ε12,400), 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 (5.77 g) 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-a7e9d7bba1f34b3eb3306280773b08ca
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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