HCID 70574824, compound → HCID 70574785, compound

HRID 1680005Notes

Reaction equation

HRID 1680005 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[C:4]=1[C:5]([NH:7][CH:8]1[C:30](=[O:31])[N:10]2[CH:11]([C:20]([O:22]CC3C=CC=CC=3)=[O:21])[C:12]3([S:19][C@H:9]12)[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[O:6]>[Pd].C(O)C>[CH3:37][O:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([NH:7][CH:8]1[C:30](=[O:31])[N:10]2[CH:11]([C:20]([OH:22])=[O:21])[C:12]3([S:19][C@H:9]12)[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[O:6]

Participants

4

Reactant 1

HCID 70574824HCID 70574824, compound

Product 1

HCID 70574785HCID 70574785, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under a hydrogen pressure of 3.2 kg/cm2 and in the presence of 1.5 g of palladium on carbon (10% Pd), a solution of 2 g (0.0038 mole) of benzyl 6-(2,6-dimethoxybenzamido)-1'-methyl-spiro[penam-2,4'-piperidine]-3-carboxylate (prepared in II.1.a) in 700 ml of ethanol is hydrogenolyzed in a Parr's apparatus for 1 hour. This is followed by filtration, the filtrate being evaporated to dryness and the residue washed with a little ethanol. 1.2 g of 6-(2,6-dimethoxybenzamido)-1'-methyl-spiro[penam-2,4'-piperidine]-3-carboxylic acid is thus obtained; yield: 60.4%; M.P. 193°-194° C. (decomposition).

Workup

  1. filtrationThis is followed by filtration
  2. customthe filtrate being evaporated to dryness
  3. washthe residue washed with a little ethanol

Sources & evidence

ORD record
ord-156a5fca92e64b5297852c7d3c20f698
Source dataset
uspto-grants-1981_06
Patent number
US04271173

Reaction notes

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