HCID 70575102, compound → HCID 70574322, compound

HRID 1680003Notes

Reaction equation

HRID 1680003 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([CH:17]([C:18]([O:20]CC3C=CC=CC=3)=[O:19])[N:16]3[C:28](=[O:40])[CH:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C@H:15]3[S:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([CH:17]([C:18]([OH:20])=[O:19])[N:16]3[C:28](=[O:40])[CH:29]([NH:30][C:31](=[O:39])[CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C@H:15]3[S:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70575102HCID 70575102, compound

Product 1

HCID 70574322HCID 70574322, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Under a hydrogen pressure of 3.2 kg/cm2 and in the presence of 4 g of palladium on carbon (10% Pd), a solution of benzyl 1'-benzyl-6-(2-phenylacetamido)-spiro[penam-2,4'-piperidine]-3-carboxylate (prepared in I.2.a) in 800 ml of ethanol is hydrogenolyzed in a Parr's apparatus for 1,5 hours, then filtered and the filtrate is evaporated to dryness in a vacuum and the residue is triturated in isopropyl alcohol. 1'-Benzyl-6-(2-phenylacetamido)-spiro[penam-2,4'-piperidine]-3-carboxylic acid is thus obtained in a yield of 71%; M.P. 170°-171° C. (decomposition).

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated to dryness in a vacuum
  3. customthe residue is triturated in isopropyl alcohol

Sources & evidence

ORD record
ord-913747ac06dc4696af08cda63f695960
Source dataset
uspto-grants-1981_06
Patent number
US04271173

Reaction notes

Loading…