Phosphorus pentachloride → HCID 131714793, compound

HRID 746322Notes

Reaction equation

HRID 746322 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[N:40]=[CH:41][N:42]([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)[CH:43]=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.Cl.[NH2:64][C@@H:65]1[C:82](=[O:83])[N:67]2[C:68]([C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])=[C:69]([CH2:73][Br:74])[CH2:70][S:71](=[O:72])[C@H:66]12.C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.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[N:40]=[CH:41][N:42]([C:44]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:43]=2)[C:33]([NH:64][C@@H:65]2[C:82](=[O:83])[N:67]3[C:68]([C:75]([O:77][C:78]([CH3:79])([CH3:80])[CH3:81])=[O:76])=[C:69]([CH2:73][Br:74])[CH2:70][S:71](=[O:72])[C@H:66]23)=[O:34])[N:31]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 15917690HCID 15917690, compoundHCID 131714794HCID 131714794, compound

Product 1

HCID 131714793HCID 131714793, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Conditions

Temperature
-10 °C

Procedure

A mixture of methylene chloride and 209 mg of phosphorus pentachloride was cooled to -10° C. 752 mg of 2-(2-tritylaminothiazol-4-yl)-2-((N-tritylimidazol-4-yl)methoxyimino)acetic acid was added to the mixture and the mixture was stirred for 10 minutes at the same temperature. 0.25 ml of triethylamine was added thereto and after 5 minutes a mixture of methylene chloride, 401 mg of tertiary butyl 7β-amino-3-bromomethyl-3-cephem-4-carboxylate 1-oxide hydrochloride and 0.14 ml of triethylamine was added to the mixture. The resulting mixture was stirred for 30 minutes at the same temperature. A 5% aqueous solution of sodium bicarbonate was added to the reaction mixture and the organic solvent layer was washed with a diluted aqueous solution of citric acid and SSC and dried with sodium sulfate and then concentrated to dryness to give 1.0 g tertiary butyl 7β-(2-(2-tritylaminothiazol-4-yl)-2-((N-tritylimidazol-4-yl)methoxyimino)acetamido)-3-bromomethyl-3-cephem-4-carboxylate 1-oxide (syn isomer).

Workup

  1. additionwas added to the mixture
  2. stirringThe resulting mixture was stirred for 30 minutes at the same temperature
  3. washthe organic solvent layer was washed with a diluted aqueous solution of citric acid and SSC
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-82780d9a6b874fa2a286705a30f4d438
Source dataset
uspto-grants-1986_07
Patent number
US04603198

Reaction notes

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