1-Azabicyclo(2.2.2)octane, 4-methyl- → HCID 178502811, compound

HRID 1253242Notes

Reaction equation

HRID 1253242 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:34]/[O:35][CH3:36])/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18][I:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[CH3:37][C:38]12[CH2:45][CH2:44][N:41]([CH2:42][CH2:43]1)[CH2:40][CH2:39]2>C(OCC)(=O)C.CO>[I-:19].[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:34]/[O:35][CH3:36])/[C:8]([NH:10][C@@H:11]2[C:32](=[O:33])[N:13]3[C:14]([C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=4)=[O:21])=[C:15]([CH2:18][N+:41]45[CH2:44][CH2:45][C:38]([CH3:37])([CH2:43][CH2:42]4)[CH2:39][CH2:40]5)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

5

Reactant 2

HCID 1426641-Azabicyclo(2.2.2)octane, 4-methyl-HCID 15671903HCID 15671903, compound

Product 1

HCID 178502811HCID 178502811, compoundYield 109.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

p-Methoxybenzyl 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-iodomethyl-3-cephem-4-carboxylate (700 mg) was dissolved in a mixed solution of ethyl acetate (50 ml) and methanol (1 ml). After the whole was ice-cooled, a solution of ethyl acetate (2.8 ml) of 4-methyl-quinuclidine (114 mg) was added thereto, and the mixture was stirred for 15 minutes. The resulting precipitate was recovered by filtration, followed by wasing with ethyl acetate to obtain p-methoxybenzyl 7β-[(Z)-2-(5-amino 1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-(4-methyl-1-quinuclidinio)methyl-3-cephem-4-carboxylate iodide (770 mg).

Workup

  1. temperaturecooled
  2. filtrationThe resulting precipitate was recovered by filtration

Sources & evidence

ORD record
ord-696e4a1ab79b4b279b72dcac8a0b2bdb
Source dataset
uspto-grants-1988_05
Patent number
US04748171

Reaction notes

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