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Acetone → 2,2,2-Trichloroethyl 2-azidomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

HRID 261246
Notes
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Reaction equation

HRID 261246 reaction equation
Br[CH2:2][C:3]1([CH3:29])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4]1.[N-:30]=[N+:31]=[N-:32].[Na+].CC(C)=O>O>[N:30]([CH2:2][C:3]1([CH3:29])[CH:7]([C:8]([O:10][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=[O:9])[N:6]2[C:16](=[O:28])[CH:17]([NH:18][C:19](=[O:27])[CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@H:5]2[S:4]1)=[N+:31]=[N-:32]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Product 1

HCID 867356172,2,2-Trichloroethyl 2-azidomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylateYield 14.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (1.08 g), sodium azide (0.26 g), acetone (20 ml) and water (4 ml) was stirred for 4 hours at room temperature. After removing acetone under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water, with a saturated sodium bicarbonate aqueous solution and further with water and then dried over sulfate. The solvent was distilled off under reduced pressure and a small amount of ether was added to the residue. Precipitated crystals were filtered off and the solvent was distilled off from the filtrate. The crystalline residue was purified by column chromatography on silica gel using chloroform as developing solvent to give 2,2,2-trichloroethyl 2-azidomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (150 mg). This substance was crystallized by adding a small amount of a mixture of ether and petroleum ether and the crystals were recrystallized from ether to give pure compound, mp 105° to 106° C.

Workup

  1. customAfter removing acetone under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water, with a saturated sodium bicarbonate aqueous solution and further with water
  4. dry with materialdried over sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. additiona small amount of ether was added to the residue
  7. customPrecipitated crystals
  8. filtrationwere filtered off
  9. distillationthe solvent was distilled off from the filtrate
  10. customThe crystalline residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-db14c13bf36041c4be0f7408c424adbe
Source dataset
uspto-grants-1979_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04164497

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes