HCID 88412251, compound → HCID 131716761, compound

HRID 704516Notes

Reaction equation

HRID 704516 reaction equation
[ClH:1].[NH2:2][CH:3]1[C:36](=[O:37])[N:5]2[C:6]([C:25]([O:27][CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])=[O:26])=[C:7]([CH2:10][S:11][C:12]3[N:17]4[N:18]=[C:19]([CH2:21][O:22][CH3:23])[N:20]=[C:16]4[N:15]=[C:14]([CH3:24])[CH:13]=3)[CH2:8][S:9][C@H:4]12.[NH2:38][C:39]1[S:40][CH:41]=[C:42](/[C:44](=[N:58]/[O:59][CH3:60])/[C:45](OSC2SC3C=CC=CC=3N=2)=[O:46])[N:43]=1>C(Cl)Cl.C(O)C>[ClH:1].[NH2:38][C:39]1[S:40][CH:41]=[C:42]([C:44](=[N:58][O:59][CH3:60])[C:45]([NH:2][CH:3]2[C:36](=[O:37])[N:5]3[C:6]([C:25]([O:27][CH2:28][O:29][C:30](=[O:35])[C:31]([CH3:33])([CH3:32])[CH3:34])=[O:26])=[C:7]([CH2:10][S:11][C:12]4[N:17]5[N:18]=[C:19]([CH2:21][O:22][CH3:23])[N:20]=[C:16]5[N:15]=[C:14]([CH3:24])[CH:13]=4)[CH2:8][S:9][C@H:4]23)=[O:46])[N:43]=1

Participants

5

Reactant 2

HCID 88412251HCID 88412251, compoundHCID 131716762HCID 131716762, compound

Product 1

HCID 131716761HCID 131716761, compoundYield 65.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

In 100 ml of methylene chloride was dissolved 11.8 g of pivaloyloxymethyl 7-amino-3-[(2-methoxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylate.hydrochloride, and 5.82 g of benzthiazolylthio 2-(2-amino-4-thiazolyl)-2-(Z)-methoxyiminoacetate was added to the solution and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with 100 ml of a 5% sodium acetate aqueous solution and further washed with water, dried over anhydrous magnesium sulfate and the solvent was distilled off. 100 ml of isopropanol containing 1.5 ml of conc. hydrochloric acid was added to the residue, and the mixture was thoroughly stirred and further stirred by adding 150 ml of ether. Then, precipitates were collected by filtration, washed with water and dried to obtain powder. This was dissolved in 50 ml of ethanol and filtered and the filtrate was added dropwise into 300 ml of ether. Precipitates were collected by filtration, washed with ether and dried to obtain 7.91 g of the title compound.

Workup

  1. additionwas added to the solution
  2. washThe reaction mixture was washed with 100 ml of a 5% sodium acetate aqueous solution
  3. washfurther washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. addition100 ml of isopropanol containing 1.5 ml of conc. hydrochloric acid was added to the residue
  7. stirringthe mixture was thoroughly stirred
  8. stirringfurther stirred
  9. additionby adding 150 ml of ether
  10. customThen, precipitates
  11. filtrationwere collected by filtration
  12. washwashed with water
  13. customdried
  14. customto obtain powder
  15. filtrationfiltered
  16. additionthe filtrate was added dropwise into 300 ml of ether
  17. customPrecipitates
  18. filtrationwere collected by filtration
  19. washwashed with ether
  20. customdried

Sources & evidence

ORD record
ord-841048684d1f4b7b9006a773da7669a1
Source dataset
uspto-grants-1991_01
Patent number
US04987129

Reaction notes

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