p-Nitrobenzyl 2,2-dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylate toluene-p-sulphonate → 2,2-Dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylic acid toluene-p-sulphonate

HRID 1154546Notes

Reaction equation

HRID 1154546 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.[CH3:12][C:13]1([CH3:40])[CH:17]([C:18]([O:20]CC2C=CC([N+]([O-])=O)=CC=2)=[O:19])[N:16]2[C:31](=[O:39])[CH:32]([NH:33][C:34]3[NH:35][CH:36]=[CH:37][N:38]=3)[C@H:15]2[S:14]1>C(O)C.C(Cl)Cl.[Pd]>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[CH3:12][C:13]1([CH3:40])[CH:17]([C:18]([OH:20])=[O:19])[N:16]2[C:31](=[O:39])[CH:32]([NH:33][C:34]3[NH:38][CH:37]=[CH:36][N:35]=3)[C@H:15]2[S:14]1

Participants

5

Reactant 1

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

Product 1

HCID 867398422,2-Dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylic acid toluene-p-sulphonate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of p-nitrobenzyl 2,2-dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylate toluene-p-sulphonate (360 mg.) in a mixture of ethanol (18 ml.) and CH2Cl2 (5 ml.) was hydrogenated at atmospheric pressure for 3 hours in the presence of 10% w/w palladium-on-carbon (180 mg.). The mixture was filtered, the filtrate evaporated and the residual yellow gum triturated with ether to give 2,2-dimethyl-6-(imidazol-2-yl)aminopenam-3-carboxylic acid toluene-p-sulphonate as a yellow solid (258 mg.) having the following n.m.r. in d6DMSO: 1.5 (s, 3H); 1.6 (s, 3H); 2.30 (s, 3H); 4.35 (s, 1H); 5.46 (d, 1H); 5.66 (d, 1H); 6.97 (s, 2H); 7.10 (d, 2H); 7.50 (d, 2H); 8.7-9.0 (br, 1H). By integration the product was 50% pure and contained 2 moles of toluene-p-sulphonic acid per mole of β-lactam.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customthe residual yellow gum triturated with ether

Sources & evidence

ORD record
ord-4b5881c391f14194ae4a4ed9cecd8e20
Source dataset
uspto-grants-1984_12
Patent number
US04490382

Reaction notes

Loading…