HCID 2835862, compound → HCID 54184965, compound

HRID 1283393Notes

Reaction equation

HRID 1283393 reaction equation
[SH:1][C:2]1[N:6]([CH3:7])[N:5]=[N:4][N:3]=1.[CH3:8][C:9]1[CH2:16][S:15][CH:14]2[N:11]([C:12](=[O:27])[CH:13]2[NH:17][C:18](=[O:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]=1[C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:34])[Cl:33])=[O:29].[Cl-].[Ca+2].[Cl-]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:7][N:6]1[C:2]([S:1][S:15][CH:14]2[N:11]([CH:10]([C:28]([O:30][CH2:31][C:32]([Cl:35])([Cl:33])[Cl:34])=[O:29])[C:9]([CH3:16])=[CH2:8])[C:12](=[O:27])[CH:13]2[NH:17][C:18](=[O:26])[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:3][N:4]=[N:5]1

Participants

6

Reactant 3

HCID 2835862HCID 2835862, compoundHCID 5284359Calcium ChlorideHCID 178482017HCID 178482017, compound

Product 1

HCID 54184965HCID 54184965, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

A solution of trichloroethyl 6β-phenylacetamido-penicillanate 1β-oxide (28.86 g) and 5-mercapto-1-methyl-tetrazole (6.96 g) in toluene (800 cc.) is heated under reflux for 3 hours, and the water formed during the reaction is removed as it is formed by passing the condensate over calcium chloride before reintroducing it into the reaction mixture. The solvent is evaporated under reduced pressure (12 mm Hg) at 40°C; the residue obtained is dissolved in chloroform (50 cc.) and the solution obtained is chromatographed on a column of silica (400 g) (0.06-0.20 mm, pH neutral; diameter of the column: 4.8 cm., height: 55 cm.). Elution is carried out using chloroform, collecting 250 cc. fractions. Fractions 10 to 17 are combined and concentrated to dryness under reduced pressure (12 mm Hg) at 40°C. 4-(1-Methyl-5-tetrazolyl-dithio)-3-phenylacetamido-1-(1-trichloroethoxycarbonyl-2-methyl-prop-2-en-1-yl)-2-azetidinone (17.4 g.) is obtained in the form of a colourless pastelike product, the characteristics of which are as follows: Rf = 0.50 [silica gel; chloroform/ethyl acetate (50/50 by volume)].

Workup

  1. temperatureunder reflux for 3 hours
  2. customis removed as it
  3. customis formed
  4. additionbefore reintroducing it into the reaction mixture
  5. customThe solvent is evaporated under reduced pressure (12 mm Hg) at 40°C
  6. customthe residue obtained
  7. customthe solution obtained
  8. customis chromatographed on a column of silica (400 g) (0.06-0.20 mm
  9. washElution
  10. customcollecting 250 cc
  11. concentrationconcentrated to dryness under reduced pressure (12 mm Hg) at 40°C

Sources & evidence

ORD record
ord-7beb014012684e7b87fbc9e775561fef
Source dataset
uspto-grants-1976_08
Patent number
US03975385

Reaction notes

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