Diazomethane → HCID 70500625, compound

HRID 1902906Notes

Reaction equation

HRID 1902906 reaction equation
[N+](=[CH2:3])=[N-].[C:4]([NH:12][CH:13]1[C:25](=[O:26])[N:15]2[C:16]([C:22]([OH:24])=[O:23])=[C:17]([CH3:21])[CH2:18][S:19](=[O:20])[C@H:14]12)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl>[C:4]([NH:12][CH:13]1[C:25](=[O:26])[N:15]2[C:16]([C:22]([O:24][CH3:3])=[O:23])=[C:17]([CH3:21])[CH2:18][S:19](=[O:20])[C@H:14]12)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 704647027-Benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide

Product 1

HCID 70500625HCID 70500625, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An excess of an ethereal diazomethane solution was added to an ice-cooled suspension of 5 gm of 7-benzamido-3-methyl-3-cephem-4-carboxylic acid-1-oxide in 150 ml of dichloromethane and the mixture was stirred for half an hour. Then, excess diazomethane was destroyed with acetic acid and methanol was added. The mixture was evaporated to dryness in vacuo and the residue was crystallized from methanol to obtain 4.5 gm (86.6% yield) of methyl 7-benzamido-3-methyl-3-cephem-4-carboxylate-1-oxide.

Workup

  1. temperaturecooled
  2. customThen, excess diazomethane was destroyed with acetic acid and methanol
  3. additionwas added
  4. customThe mixture was evaporated to dryness in vacuo
  5. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-71dbe44d8fb844349aab7616008a9569
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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