HCID 11814484, compound → HCID 9845231, compound

HRID 617893Notes

Reaction equation

HRID 617893 reaction equation
C([O:8][P:9]([CH2:19][C:20]1([C:25]([NH:27][C@H:28]2[CH2:34][CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[N:30]([CH2:39][C:40]([O:42]CC3C=CC=CC=3)=[O:41])[C:29]2=[O:50])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1)([O:11]CC1C=CC=CC=1)=[O:10])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[P:9]([CH2:19][C:20]1([C:25]([NH:27][C@H:28]2[CH2:34][CH2:33][C:32]3[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=3[N:30]([CH2:39][C:40]([OH:42])=[O:41])[C:29]2=[O:50])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1)([OH:10])([OH:11])=[O:8]

Participants

5

Reactant 2

HCID 11814484HCID 11814484, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9845231HCID 9845231, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.9 g of benzyl (3S)-3-(1-dibenzylphosphonomethylcyclopentane-1-carbonylamino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate (preparation see Example 1G) were dissolved in 100 ml of ethanol. 1.2 g of a 5% strength palladium catalyst on active carbon were added to the solution and it was hydrogenated for 3 hours at a hydrogen pressure of 5.5 bar. For workup, the catalyst was filtered out, the filtrate was evaporated in vacuo and the residue was dried. 0.9 g of the title compound was obtained as a foamy product, IR: 3400, 1720, 1630 cm-1 (KBr); [α]D20 =-140.8° (c=0.5 in methanol).

Workup

  1. filtrationFor workup, the catalyst was filtered out
  2. customthe filtrate was evaporated in vacuo
  3. customthe residue was dried

Sources & evidence

ORD record
ord-309ac4de1dfe47768efabc2a132a38bb
Source dataset
uspto-grants-1999_09
Patent number
US05952327

Reaction notes

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