HCID 70577004, compound → HCID 70574870, compound

HRID 1680002Notes

Reaction equation

HRID 1680002 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH:11]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])[N:10]3[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:9]3[S:8]2)[CH2:4][CH2:3]1>[Pd].C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH:11]([C:12]([OH:14])=[O:13])[N:10]3[C:22](=[O:34])[CH:23]([NH:24][C:25](=[O:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:9]3[S:8]2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 70577004HCID 70577004, compound

Product 1

HCID 70574870HCID 70574870, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under a hydrogen pressure of 3.2 kg/cm2 and in the presence of 4.4 g of palladium on carbon (10% Pd), a solution of 4.4 g (0.091 mole) of benzyl 1'-methyl-6-(2-phenylacetamido)-spiro[penam-2,4'-piperidine]-3-carboxylate prepared in I.1.a) in 800 ml of ethanol are hydrogenolyzed in a Parr's apparatus for 1 hour. After filtering, the precipitate is digested in 1.5 liter of a 9:1 v/v methanol-water mixture for 1 hour. Evaporation of the filtrate to dryness gives 1.6 g of 1'-methyl-6-(2-phenylacetamido)-spiro[penam-2,4'-piperidine]-3-carboxylic acid. Yield: 44.8%; M.P. 189°-190° C. (decomposition).

Workup

  1. filtrationAfter filtering
  2. waitthe precipitate is digested in 1.5 liter of a 9:1 v/v methanol-water mixture for 1 hour
  3. customEvaporation of the filtrate to dryness

Sources & evidence

ORD record
ord-16f2aab4803c4d52bc6230f232dd40c6
Source dataset
uspto-grants-1981_06
Patent number
US04271173

Reaction notes

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