Triethylamine → 3-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 442357Notes

Reaction equation

HRID 442357 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:15]([OH:17])=O)[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH3:18][C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][C@@H:26]2[C@H:27]([NH2:30])[C:28](=[O:29])[N:25]2[C:24]=1[C:33]([OH:35])=[O:34])=[O:20].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37]>C(Cl)Cl.C(O)CC>[CH2:36]([NH+:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH3:37].[C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][CH:26]2[N:25]([C:28](=[O:29])[CH:27]2[NH2:30])[C:24]=1[C:33]([O-:35])=[O:34])(=[O:20])[CH3:18].[C:19]([O:21][CH2:22][C:23]1[CH2:32][S:31][CH:26]2[N:25]([C:28](=[O:29])[CH:27]2[NH:30][C:15](=[O:17])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][N:1]=[N+:2]=[N-:3])=[CH:10][CH:9]=2)[C:12]([OH:14])=[O:13])[C:24]=1[C:33]([OH:35])=[O:34])(=[O:20])[CH3:18]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 4413287-Aminocephalosporanic acid2×HCID 22767759p-Azidomethylphenylmalonic acid

Product 2

HCID 227677693-[(Acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 1317101243-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid triethylammonium salt

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Procedure

α-Carboxy-p-azidomethylphenylacetyl nitrophenyl polymer, prepared according to the procedure described in Canadian Pat. No. 892,580, carrying 4 m. mole of p-azidomethylphenylmalonic acid was suspended for 8 hours in 20 ml of dry methylene chloride solution containing 1 m. mole of 3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid triethylammonium salt, which is prepared from 544 mg of 7-aminocephalosporanic acid (1 m. mole) and 0.56 ml of triethylamine (1 m. mole) at room temperature. After only traces of 7-aminocephalosporanic acid remain in solution, which is determined by thin layer chromatography on cellulose in 70% aqueous propanol, the polymer was filtered off and washed with 3 portions of 5- ml each of methylene chloride. The combined filtrates were evaporated and the residue was dissolved in 20 ml of distilled water. This solution was acidified to pH 2 by adding 0.2 normal hydrochloric acid and extracted with ethyl acetate. The organic solution was dried over sodium sulfate and evaporated at room temperature. The remaining soldi was dried overnight over phosphorus pentoxide under vacuum to give 3-[(acetyloxy)methyl] -7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Workup

  1. customα-Carboxy-p-azidomethylphenylacetyl nitrophenyl polymer, prepared
  2. additioncontaining 1 m
  3. filtrationthe polymer was filtered off
  4. washwashed with 3 portions of 5- ml each of methylene chloride
  5. customThe combined filtrates were evaporated
  6. dissolutionthe residue was dissolved in 20 ml of distilled water
  7. additionby adding 0.2 normal hydrochloric acid
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic solution was dried over sodium sulfate
  10. customevaporated at room temperature
  11. dry with materialThe remaining soldi was dried overnight over phosphorus pentoxide under vacuum

Sources & evidence

ORD record
ord-4bfcc65514bf4a2e826103dc724b854e
Source dataset
uspto-grants-1977_08
Patent number
US04045438

Reaction notes

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