Water → HCID 131716118, compound

HRID 1607940Notes

Reaction equation

HRID 1607940 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]=[C:9]([C:41]1[N:42]=[C:43]([NH:46][C:47]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[S:44][CH:45]=1)[C:10]([NH:12][CH:13]1[C:39](=[O:40])[N:15]2[C:16]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:17]([CH2:21]Cl)[CH2:18][S:19](=[O:20])[C@H:14]12)=[O:11].[I-:66].[Na+].C(O[CH2:72][CH3:73])(=O)C.O>CC(C)=O>[I-:66].[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]=[C:9]([C:41]1[N:42]=[C:43]([NH:46][C:47]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)([C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[S:44][CH:45]=1)[C:10]([NH:12][CH:13]1[C:39](=[O:40])[N:15]2[C:16]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:17]([CH2:21][N+:12]3([CH3:13])[CH2:73][CH2:72][CH2:9][CH2:10]3)[CH2:18][S:19](=[O:20])[C@H:14]12)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 131716116HCID 131716116, compound

Product 1

HCID 131716118HCID 131716118, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of benzhydryl 7-[2-(2-tetrahydropyranyl)oxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) in acetone (100 ml) was added sodium iodide (2.5 g) under ice-cooling. The mixture was stirred for 4.5 hours at the same temperature and then poured into a mixure of ethyl acetate (150 ml) and water (150 ml). The organic layer was separated, washed with brine and dried over magnesium sulfate. The solvent was distilled off. To the residue was added tetrahydrofuran (25 ml) and then 1-methylpyrrolidine (0.52 ml) was added thereto under cooling. The mixture was stirred for 1 hour at the same temperature and then the mixture was poured into ice-water. The resulting precipitates were collected by filtration, dried over phosphorus pentoxide and then subjected to column chromatography on silica gel using methylene chloride and methanol (5:2) as an eluent. The fractions containing the object compound were collected and evaporated to give benzhydryl 7-[2-(2-tetrahydropyranyl)oxyimino-2-(2 -tritylaminothiazol-4-yl)acetamido]-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate-1-oxide iodide (syn isomer) (1.0 g).

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. additionTo the residue was added tetrahydrofuran (25 ml)
  7. addition1-methylpyrrolidine (0.52 ml) was added
  8. temperatureunder cooling
  9. stirringThe mixture was stirred for 1 hour at the same temperature
  10. additionthe mixture was poured into ice-water
  11. customThe resulting precipitates
  12. filtrationwere collected by filtration
  13. dry with materialdried over phosphorus pentoxide
  14. additionThe fractions containing the object compound
  15. customwere collected
  16. customevaporated

Sources & evidence

ORD record
ord-df6ca6a68835451d9988dfa1df4c9dce
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

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