2-Fluoro-1H-benzimidazole → HCID 86739840, compound

HRID 1154544Notes

Reaction equation

HRID 1154544 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:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[C:17]([CH3:20])([CH3:19])[S:18][C@H:14]12.F[C:27]1[NH:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>CN(C=O)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.[N:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[NH:31][C:27]=1[NH:12][CH:13]1[C:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[C:17]([CH3:20])([CH3:19])[S:18][C@H:14]12

Participants

4

Reactant 2

HCID 130720952-Fluoro-1H-benzimidazoleHCID 86739841HCID 86739841, compound

Product 1

HCID 86739840HCID 86739840, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of anhydrous 6-amino-2,2-dimethylpenam-3-carboxylic acid toluene-p-sulphonate (171 mg.) in dry DMF was added 2-fluorobenzimidazole (150 mg.) in one portion and the mixture stirred at ambient temperature for 1.5 hours. The mixture was evaporated to dryness under reduced pressure at room temperature and the resulting residue, a mobile oil, was triturated with EtOAc (2×10 ml.) and then dry acetonitrile (2 ml.) whereupon the product crystallised. The solid was filtered and washed with acetonitrile and ether to give 6-(benzimidazol-2-yl)amino-2,2-dimethylpenam-3-carboxylic acid toluene-p-sulphonate (185 mg.), m.p. 181°-183°, having the following n.m.r. spectrum in d6DMSO: 1.49 (s, 3H); 1.62 (s, 3H); 2.29 (s, 3H); 4.39 (s, 1H); 5.54 (br, 1H); 5.68 (d, 1H); 7.0-7.56 (m, 8H); 9.93 (br, 1H).

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure at room temperature
  2. customthe resulting residue, a mobile oil, was triturated with EtOAc (2×10 ml.)
  3. customdry acetonitrile (2 ml.) whereupon the product crystallised
  4. filtrationThe solid was filtered
  5. washwashed with acetonitrile and ether

Sources & evidence

ORD record
ord-0a439c3766634e39abd8bb2389e77baa
Source dataset
uspto-grants-1984_12
Patent number
US04490382

Reaction notes

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