Methyl iodide →

HRID 1682446Notes

Reaction equation

HRID 1682446 reaction equation
[C:1]([O:20][N:21]=[C:22]([C:60]1[N:61]=[C:62]([NH:65][C:66]([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)([C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)[C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[S:63][CH:64]=1)[C:23]([NH:25][CH:26]1[C:58](=[O:59])[N:28]2[C:29]([C:42]([O:44][CH:45]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)=[O:43])=[C:30]([CH:33]=[CH:34][S:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH2:31][S:32][C@H:27]12)=[O:24])([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:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:85][I:86]>C(#N)C.C(Cl)Cl>[I-:86].[C:1]([O:20][N:21]=[C:22]([C:60]1[N:61]=[C:62]([NH:65][C:66]([C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)([C:79]2[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=2)[C:73]2[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=2)[S:63][CH:64]=1)[C:23]([NH:25][CH:26]1[C:58](=[O:59])[N:28]2[C:29]([C:42]([O:44][CH:45]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)=[O:43])=[C:30]([CH:33]=[CH:34][S:35][CH2+:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]3[CH3:85])[CH2:31][S:32][C@H:27]12)=[O:24])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 131720030HCID 131720030, compound

Product 0

No Product data yet.

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7-[2-trityloxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[2-(2-pyridyl)thiovinyl]-3-cephem-4-carboxylate (2.4 g) in a mixture of acetonitrile (12 ml) and methylene chloride (4.8 ml) was added methyl iodide (18.7 ml) and the mixture was stirred at room temperature for 3 days. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in chloroform (38 ml) and dripped into diisopropyl ether (120 ml). The resultant precipitate was recovered to provide benzhydryl 7-[2-trityloxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[2-(1-methyl-2-pyridinio)thiovinyl]-3-cephem-4-carboxylate iodide (3.5 g).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (38 ml)
  4. customThe resultant precipitate was recovered

Sources & evidence

ORD record
ord-ddf3ef19cb5046c9bcf56dc7822bf266
Source dataset
uspto-grants-1997_06
Patent number
US05635500

Reaction notes

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