Triethylamine → Penicillanic Acid

HRID 1277731Notes

Reaction equation

HRID 1277731 reaction equation
[CH3:1][C:2]1([CH3:14])[S:6][C@@H:5]2[C@H:7](N)[C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=[O:12].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1([CH3:14])[S:6][C@@H:5]2[CH2:7][C:8](=[O:9])[N:4]2[C@H:3]1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 110826-Aminopenicillanic acid

Product 1

HCID 6891Penicillanic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.16 g 6-amino-penicillanic acid were added to 20 ml methylene chloride cooled to +5° C. Then, 2 g triethylamine were added and the mixture was stirred for 2 hours at +5° C. Then, at 0° C. 10 ml methylene chloride were added, in which 2.6 g compound of formula (III) obtained in Example 6 were dissolved. Then, the mixture was stirred for 30 minutes at +5° C., the solvent was vacuum evaporated and the residue was dissolved in 10 ml methyl-ethyl-ketone. Then, 1.9 g para-toluensulphonic acid dissolved in 10 ml methyl-ethyl-ketone were added. The solid thus formed was filtered and crystallized from a mixture acetone-water.

Workup

  1. temperaturecooled to +5° C
  2. customat 0° C
  3. dissolutionwere dissolved
  4. stirringThen, the mixture was stirred for 30 minutes at +5° C.
  5. customevaporated
  6. dissolutionthe residue was dissolved in 10 ml methyl-ethyl-ketone
  7. dissolutionThen, 1.9 g para-toluensulphonic acid dissolved in 10 ml methyl-ethyl-ketone
  8. additionwere added
  9. customThe solid thus formed
  10. filtrationwas filtered
  11. customcrystallized from a mixture acetone-water

Sources & evidence

ORD record
ord-cd177923e7014f678aaae240d22cb53b
Source dataset
uspto-grants-1981_07
Patent number
US04278792

Reaction notes

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