HCID 178430889, compound → HCID 178430890, compound

HRID 1154548Notes

Reaction equation

HRID 1154548 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([CH3:41])[CH:17]([C:18]([O:20]CC2C=CC([N+]([O-])=O)=CC=2)=[O:19])[N:16]2[C:31](=[O:40])[CH:32]([NH:33][C:34]3[NH:35][CH:36]=[C:37]([CH3:39])[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([CH3:41])[CH:17]([C:18]([OH:20])=[O:19])[N:16]2[C:31](=[O:40])[CH:32]([NH:33][C:34]3[NH:35][CH:36]=[C:37]([CH3:39])[N:38]=3)[C@H:15]2[S:14]1

Participants

5

Reactant 1

HCID 178430889HCID 178430889, compound

Product 1

HCID 178430890HCID 178430890, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of p-nitrobenzyl 2,2-dimethyl-6-(4-methylimidazol-2-yl)aminopenam-3-carboxylate toluene-p-sulphonate (200 mg.) and 10% w/w palladium-on-carbon in ethanol (12 ml.) and methylene chloride (3 ml.) was shaken under hydrogen at atmospheric pressure for 3.5 hours. The mixture was filtered, the filtrate evaporated to dryness and the residual gum triturated with ether to give 2,2-dimethyl-6-(4-methylimidazol-2-yl)aminopenam-3-carboxylic acid toluene-p-sulphonate as a yellow powder (118 mg.) having the following n.m.r. in d6DMSO+CD3COOD: 1.5 (s, 3H); 1.6 (s, 3H); 2.11 (s, 3H); 2.3 (s, 3H); 4.35 (s, 1H); 5.40 (d, 1H); 5.62 (d, 1H); 6.72 (s, 1H); 7.1 (d, 2H); 7.5 (d, 2H); 8.76 (s, 1H). The sample was approximately 50% pure.

Workup

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

Sources & evidence

ORD record
ord-0db87fc95cef49e9b990b237e3d99978
Source dataset
uspto-grants-1984_12
Patent number
US04490382

Reaction notes

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