Phenylacetyl chloride → HCID 12895273, compound

HRID 1730904Notes

Reaction equation

HRID 1730904 reaction equation
[C:1]([C:4]1[CH:35]=[CH:34][CH:33]=[CH:32][C:5]=1[C:6]([NH:8][CH:9]1[C:30](=[O:31])[N:11]2[C:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])=[C:13]([CH3:16])[CH2:14][S:15][C@H:10]12)=[O:7])(O)=O.C(N(CC)CC)C.ClC(OCC)=O.NN.C1(CC(Cl)=O)C=CC=CC=1>O1CCCC1>[C:32]1([CH2:5][C:6]([NH:8][CH:9]2[C:30](=[O:31])[N:11]3[C:12]([C:17]([O:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=4)=[O:18])=[C:13]([CH3:16])[CH2:14][S:15][C@H:10]23)=[O:7])[CH:33]=[CH:34][CH:35]=[CH:4][CH:1]=1

Participants

7

Reactant 5

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 9321HydrazineHCID 10928Ethyl chloroformateHCID 70633064HCID 70633064, compound

Product 1

HCID 12895273HCID 12895273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of p-nitrobenzyl 7-(2-carboxybenzamido)-3-methyl-3-cephem-4-carboxylate (462 mg., 1 mmol.) in tetrahydrofuran at 0° C. is added triethylamine (0.14 ml., 1 mmol.). After 15 minutes, ethyl chloroformate (0.1 ml., 2 mmol.) is added, and then after 0.5 hour at 0° C., anhydrous hydrazine (0.03 ml., 1 mmol.) is added to the reaction mixture. After 15 minutes, the mixture is filtered, and the filtrate is evaporated to dryness in vacuo. The residue is taken up in acetone (15 ml.) and tetrahydrofuran (15 ml.), and phenylacetyl chloride (0.13 ml., 1 mmol.) is added. After refluxing for 30 min., the mixture is cooled and evaporated in vacuo to dryness. The produce is taken up in chloroform (50 ml.) and washed successively with 1N HCl (30 ml.), 10% sodium bicarbonate (40 ml.), and brine (40 ml.), dried over MgSO4, and evaporated in vacuo to dryness. The colorless product is slurried with ethyl acetate (12 ml.). Filtration gives p-nitrobenzyl 7-phenylacetamido-3-methyl-3-cephem-4-carboxylate. Recrystallization from ethyl acetate gives an analytical sample: m.p. 227°-230°.

Workup

  1. waitafter 0.5 hour at 0° C.
  2. waitAfter 15 minutes
  3. filtrationthe mixture is filtered
  4. customthe filtrate is evaporated to dryness in vacuo
  5. temperatureAfter refluxing for 30 min.
  6. temperaturethe mixture is cooled
  7. customevaporated in vacuo to dryness
  8. washwashed successively with 1N HCl (30 ml.), 10% sodium bicarbonate (40 ml.), and brine (40 ml.)
  9. dry with materialdried over MgSO4
  10. customevaporated in vacuo to dryness
  11. filtrationFiltration

Sources & evidence

ORD record
ord-6e6f690a68ca43f593ab4f63e1a9ad78
Source dataset
uspto-grants-1976_11
Patent number
US03994888

Reaction notes

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