Triethylamine → HCID 131714792, compound

HRID 746321Notes

Reaction equation

HRID 746321 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:36][O:37][CH2:38][C:39]2[CH:43]=[CH:42][N:41]([C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[N:40]=2)[C:33](O)=[O:34])[N:31]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.Cl.[NH2:71][C@@H:72]1[C:89](=[O:90])[N:74]2[C:75]([C:82]([O:84][C:85]([CH3:88])([CH3:87])[CH3:86])=[O:83])=[C:76]([CH2:80][Br:81])[CH2:77][S:78](=[O:79])[C@H:73]12>C(Cl)(Cl)Cl.C(Cl)Cl>[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:36][O:37][CH2:38][C:39]2[CH:43]=[CH:42][N:41]([C:44]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[N:40]=2)[C:33]([NH:71][C@@H:72]2[C:89](=[O:90])[N:74]3[C:75]([C:82]([O:84][C:85]([CH3:86])([CH3:87])[CH3:88])=[O:83])=[C:76]([CH2:80][Br:81])[CH2:77][S:78](=[O:79])[C@H:73]23)=[O:34])[N:31]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 24819Phosphorus pentachlorideHCID 15917690HCID 15917690, compoundHCID 53739979HCID 53739979, compound

Product 1

HCID 131714792HCID 131714792, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

420 mg of phosphorus pentachloride was dissolved in 70 ml of chloroform and the mixture was cooled to -25° to -30° C. 1.51 g of 2-(2-tritylaminothiazol-4-yl)-2-((N-tritylpyrazol-3-yl)methoxyimino)acetic acid was added to the mixture and the resulting mixture was stirred for 30 minutes at the same temperature. 0.5 ml of triethylamine was added to the mixture and, after 3 minutes, a mixture of 810 mg of tertiary butyl 7β-amino-3-bromomethyl-3-cephem-4-carboxylate 1-oxide hydrochloride, 0.28 ml of triethylamine and methylene chloride was added to the mixture. The resulting mixture was stirred for 40 minutes at the same temperature. 50 ml of chloroform cooled in an ice-bath was added to the reaction mixture and the mixture was washed with water, a 3% aqueous solution of sodium bicarbonate and SSC and dried with sodium sulfate and then concentrated to dryness. The residue was purified by silica gel column chromatography using chloroform and nextly a mixture of chloroform and ethyl acetate (4:1 by volume) as an eluent solvent to give 1.92 g of tertiary butyl 7β-(2-(2-tritylaminothiazol-4-yl)-2-((N-tritylpyrazol-3-yl)methoxyimino)acetamido)-3-bromomethyl-3-cephem-4-carboxylate 1-oxide (syn isomer).

Workup

  1. temperaturethe mixture was cooled to -25° to -30° C
  2. additionwas added to the mixture
  3. stirringThe resulting mixture was stirred for 40 minutes at the same temperature
  4. additionwas added to the reaction mixture
  5. washthe mixture was washed with water
  6. dry with materiala 3% aqueous solution of sodium bicarbonate and SSC and dried with sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by silica gel column chromatography
  9. additionnextly a mixture of chloroform and ethyl acetate (4:1 by volume) as an eluent solvent

Sources & evidence

ORD record
ord-cd33d61481274a6cbcf509e0e1da328e
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

Loading…