Ampicillin → HCID 20314220, compound

HRID 1283050Notes

Reaction equation

HRID 1283050 reaction equation
[CH:1]([N:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8])=[O:2].C(N(CC)CC)C.C[Si](C)(C)[Cl:18].CC1(C)S[C@@H]2[C@H](NC([C@H](N)C3C=CC=CC=3)=O)C(=O)N2[C@H]1[C:41]([OH:43])=O>C1C=CC=CC=1>[CH:1]([N:3]1[CH2:7][CH2:6][N:5]([C:41]([Cl:18])=[O:43])[C:4]1=[O:8])=[O:2]

Participants

6

Reactant 4

HCID 6249AmpicillinHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 12771232HCID 12771232, compound

Product 1

HCID 20314220HCID 20314220, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of N-formyl-imidazolidin-2-one (6.0 parts by weight), benzene (40 parts by volume) and triethylamine (11.8 parts by volume) was boiled under reflux and at the same time a solution of trimethylchlorosilane (8.5 parts by weight) in benzene (20 parts by volume) was added dropwise. Thereafter the mixture was boiled for a further 5 hours and then left to stand overnight at room temperature and the precipitate present was filtered off and washed with benzene. The combined benzene solutions, on standing overnight, formed further amounts of precipitate which were filtered off. A solution of phosgene (15.6 parts by weight) in dichloromethane (30 parts by volume) was then added dropwise to the filtrate and the mixture was subsequently left to stand overnight in a refrigerator. It was then completely evaporated to dryness in a rotary evaporator. The residue, a mass which did not crystallize throughout to give a solid, was used, as it was, for the reaction with ampicillin.

Workup

  1. additionwas added dropwise
  2. waitleft
  3. waitto stand overnight at room temperature
  4. filtrationthe precipitate present was filtered off
  5. washwashed with benzene
  6. waitThe combined benzene solutions, on standing overnight
  7. customformed further amounts of precipitate which
  8. filtrationwere filtered off
  9. additionA solution of phosgene (15.6 parts by weight) in dichloromethane (30 parts by volume) was then added dropwise to the filtrate
  10. waitthe mixture was subsequently left
  11. waitto stand overnight in a refrigerator
  12. customIt was then completely evaporated to dryness in a rotary evaporator
  13. customThe residue, a mass which did not crystallize throughout
  14. customto give a solid

Sources & evidence

ORD record
ord-ff78338af76049d7af9052d47e447751
Source dataset
uspto-grants-1976_08
Patent number
US03974142

Reaction notes

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