HCID 86737764, compound → HCID 86737766, compound

HRID 1680019Notes

Reaction equation

HRID 1680019 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.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[NH2:23][CH:24]1[C:46](=[O:47])[N:26]2[CH:27]([C:36]([O:38]CC3C=CC=CC=3)=[O:37])[C:28]3([S:35][C@H:25]12)[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3.[H][H]>C(O)C.[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.[C:12]1([CH3:22])[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=1.[NH2:23][CH:24]1[C:46](=[O:47])[N:26]2[CH:27]([C:36]([OH:38])=[O:37])[C:28]3([S:35][C@H:25]12)[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3

Participants

5

Reactant 2

HCID 86737764HCID 86737764, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86737766HCID 86737766, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2.5 g (0.00354 mole) of benzyl 6-amino-1'-methyl-spiro[penam-2,4'-piperidine]-3-carboxylate di-p-toluenesulfonate (obtained in 8.1) in 1.5 liter of ethanol is subjected to hydrogenolysis in a Parr's apparatus under 3.2 kg/cm2 of hydrogen in the presence of 2 g of palladium on carbon (10% Pd). After 90 minutes, the reaction mixture is filtered and the filtrate is evaporated to dryness and lyophilized in 600 ml of water. 1.8 g of 6-amino-1'-methyl-spiro[penam-2,4'-piperidine]-3-carboxylic acid di-p-toluenesulfonate is obtained; yield: 83%; M.P. approx 155°-160° C. (start of decomposition).

Workup

  1. filtrationthe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-7ba6bfc2bfb74a938598d378f8421aa3
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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