2-Fluoro-1H-imidazole → p-Nitrobenzyl 2,2-dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylate toluene-p-sulphonate

HRID 1154547Notes

Reaction equation

HRID 1154547 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][CH:13]1[C:34](=[O:35])[N:15]2[CH:16]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:17]([CH3:20])([CH3:19])[S:18][C@H:14]12.F[C:37]1[NH:38][CH:39]=[CH:40][N:41]=1>C(#N)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[CH3:19][C:17]1([CH3:20])[CH:16]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)=[O:22])[N:15]2[C:34](=[O:35])[CH:13]([NH:12][C:37]3[NH:38][CH:39]=[CH:40][N:41]=3)[C@H:14]2[S:18]1

Participants

4

Reactant 2

HCID 5595422-Fluoro-1H-imidazoleHCID 86739845p-Nitrobenzyl 6-amino-2,2-dimethylpenam-3-carboxylate toluene-p-sulphonate

Product 1

HCID 86739843p-Nitrobenzyl 2,2-dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylate toluene-p-sulphonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of p-nitrobenzyl 6-amino-2,2-dimethylpenam-3-carboxylate toluene-p-sulphonate (523 mg.) and 2-fluoroimidazole (100 mg.) in acetonitrile (2 ml.) was stirred at 50° for 3 hours. The resulting solution was evaporated to dryness and the residue obtained was triturated with ether to give p-nitrobenzyl 2,2-dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylate toluene-p-sulphonate as a 50% pure solid (572 mg.) which was used without further purification.

Workup

  1. customThe resulting solution was evaporated to dryness
  2. customthe residue obtained
  3. customwas triturated with ether

Sources & evidence

ORD record
ord-30acf8c1cf4546e38653bba4094b7330
Source dataset
uspto-grants-1984_12
Patent number
US04490382

Reaction notes

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