Triethylamine → HCID 70542433, compound

HRID 2285628Notes

Reaction equation

HRID 2285628 reaction equation
C(N(CC)CC)C.[C:8]1([CH2:14][C:15]([NH:17][C@@H:18]2[C:30](=[O:31])[N:20]3[C:21]([C:27]([OH:29])=[O:28])=[C:22]([CH2:25][OH:26])[CH2:23][S:24][C@H:19]23)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH2:39]=[C:40]1[O:44][C:42](=[O:43])[CH2:41]1>ClCCl>[C:8]1([CH2:14][C:15]([NH:17][C@@H:18]2[C:30](=[O:31])[N:20]3[C:21]([C:27]([OH:29])=[O:28])=[C:22]([CH2:25][O:26][C:42](=[O:43])[CH2:41][C:40](=[O:44])[CH3:39])[CH2:23][S:24][C@H:19]23)=[O:16])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 705426117beta-Phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylic acid triethylamine salt

Product 1

HCID 70542433HCID 70542433, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (50 ml) was dissolved 7β-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylic acid triethylamine salt (4.49 g) and, at room temperature, triethylamine (0.51 g) and diketene (1.26 g) were added. The reaction was conducted for 2 hours, after which time the solvent was distilled off under reduced pressure. The residue was diluted with water and adjusted to pH 6.0. This aqueous solution was extracted twice with ethyl acetate, brought down to pH 2.0 with 4 N-HCl and extracted three times with ethyl acetate. The ethyl acetate solution was washed with a saturated aqueous solution of sodium chloride, treated with magnesium sulfate and filtered. The solvent was distilled off under reduced pressure and the residue was recrystallized from ethyl acetate-ether. The above procedure provided 7β-phenylacetamido-3-(3-oxobutyryloxy)methyl-3-cephem-4-carboxylic acid (4.16 g) (yield 96.3%).

Workup

  1. distillationafter which time the solvent was distilled off under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionThis aqueous solution was extracted twice with ethyl acetate
  4. extractionextracted three times with ethyl acetate
  5. washThe ethyl acetate solution was washed with a saturated aqueous solution of sodium chloride
  6. additiontreated with magnesium sulfate
  7. filtrationfiltered
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-75398ec9c2a04cb39402a945dcd95d80
Source dataset
uspto-grants-1982_04
Patent number
US04323676

Reaction notes

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