2,2-Dimethyl-5-(3-thienyl)-1,3-dioxane-4,6-dione → HCID 178477386, compound

HRID 1833411Notes

Reaction equation

HRID 1833411 reaction equation
[NH2:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]([S:11][C:12]3[NH:16][N:15]=[N:14][N:13]=3)[CH3:10])[CH2:7][S:8][C@H:3]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.CC1(C)[O:40][C:39](=O)[CH:38]([C:42]2[CH:46]=[CH:45][S:44][CH:43]=2)[C:37](=[O:47])[O:36]1>O1CCCC1>[C:37]([CH:38]([C:42]1[CH:46]=[CH:45][S:44][CH:43]=1)[C:39]([NH:1][CH:2]1[C:20](=[O:21])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]([S:11][C:12]3[NH:13][N:14]=[N:15][N:16]=3)[CH3:10])[CH2:7][S:8][C@H:3]12)=[O:40])([OH:47])=[O:36]

Participants

5

Reactant 3

HCID 3703012,2-Dimethyl-5-(3-thienyl)-1,3-dioxane-4,6-dioneHCID 11708267BistrimethylsilylacetamidHCID 1784773817-Amino-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 178477386HCID 178477386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 656.7 mg (2 mmol) of 7-amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (as prepared in example 9) in 25 ml. of anhydrous tetrahydrofuran there is added 1.6 ml. of bis-trimethylsilylacetamide. The mixture is stirred to give a solution to which there is added at once 452.5 mg (2 mmol) of 2.2-dimethyl-5-(3-thienyl)-1.3-dioxane-4.6-dione as prepared in example 6, the mixture being stirred at 25° C for 8 hours. Tetrahydrofuran is removed under reduced pressure and the residue is taken up with 30 ml. of water, brought to pH 2.5 with 0.5 ml. 6N HCl, stirred for 15 minutes and extracted three times with 25 ml. of ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and filtered over DARCO G60 (a product manufactured and sold by Atlas Chem. Ind.)-charcoal. Most of the solvent is evaporated under reduced pressure and 100 ml. of petroleum ether (50°-70° C) is added thereto. The suspension is stirred for 30 minutes and filtered. The precipitate is washed with 20 ml. of petroleum ether (50°-70° C) and dried over anhydrous P2O5 under reduced pressure to yield DL-7-[α-carboxy-α-(3-thienyl)-acetamido]-3-(1-methyl-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (RIT 3838).

Workup

  1. customto give a solution to which there
  2. customas prepared in example 6
  3. stirringthe mixture being stirred at 25° C for 8 hours
  4. customTetrahydrofuran is removed under reduced pressure
  5. stirring6N HCl, stirred for 15 minutes
  6. extractionextracted three times with 25 ml
  7. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  8. filtrationfiltered over DARCO G60 (a product
  9. customMost of the solvent is evaporated under reduced pressure and 100 ml
  10. additionof petroleum ether (50°-70° C) is added
  11. stirringThe suspension is stirred for 30 minutes
  12. filtrationfiltered
  13. washThe precipitate is washed with 20 ml
  14. dry with materialof petroleum ether (50°-70° C) and dried over anhydrous P2O5 under reduced pressure

Sources & evidence

ORD record
ord-5045a8d973624234b63a92f86ab4f5bc
Source dataset
uspto-grants-1978_01
Patent number
US04066664

Reaction notes

Loading…