2-Fluoro-1H-benzimidazole → HCID 86739837, compound

HRID 1154543Notes

Reaction equation

HRID 1154543 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:32](=[O:33])[N:15]2[CH:16]([C:21]([O:23][CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[O:22])[C:17]([CH3:20])([CH3:19])[S:18][C@H:14]12.F[C:35]1[NH:36][C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[N:39]=1>C(Cl)Cl>[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:36]1[C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[NH:39][C:35]=1[NH:12][CH:13]1[C:32](=[O:33])[N:15]2[CH:16]([C:21]([O:23][CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:28])([CH3:30])[CH3:29])=[O:22])[C:17]([CH3:19])([CH3:20])[S:18][C@H:14]12

Participants

4

Reactant 2

HCID 130720952-Fluoro-1H-benzimidazoleHCID 86739839HCID 86739839, compound

Product 1

HCID 86739837HCID 86739837, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of pivaloyloxymethyl 6-amino-2,2-dimethylpenam-3-carboxylate toluene-p-sulphonate (200 mg.) and 2-fluorobenzimidazole (108 mg.) in methylene chloride (2 ml.) was stirred at ambient temperature for 3 hours. The reaction mixture was evaporated to dryness and the residue was triturated with ether and hexane to give pivaloyloxymethyl 6-(benzimidazol-2-yl)amino-2,2-dimethylpenam-3-carboxylate toluene-p-sulphonate (170 mg.) as a solid which had the following n.m.r. spectrum in d6DMSO: 1.14 (s, 9H); 1.43 (s, 3H); 1.60 (s, 3H); 2.24 (s, 3H); 4.55 (s, 1H); 5.5-5.9 (m, 4H); 7.0-7.54 (m, 8H).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was triturated with ether and hexane

Sources & evidence

ORD record
ord-187ce44b19884252a7b638c48c815f77
Source dataset
uspto-grants-1984_12
Patent number
US04490382

Reaction notes

Loading…