HCID 11548492, compound → HCID 21849082, compound

HRID 2293053Notes

Reaction equation

HRID 2293053 reaction equation
[ClH:1].C(OC([NH:12][CH:13]([C:30]1[CH:35]=[CH:34][C:33]([C:36](=[NH:38])[NH2:37])=[CH:32][CH:31]=1)[P:14]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:22])[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O)C1C=CC=CC=1.[H][H]>CO.Cl.[Pd]>[ClH:1].[ClH:1].[NH2:12][CH:13]([C:30]1[CH:35]=[CH:34][C:33]([C:36](=[NH:37])[NH2:38])=[CH:32][CH:31]=1)[P:14]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:22])[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 11548492HCID 11548492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21849082HCID 21849082, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

A sample of 1.8 g of diphenyl N-benzyloxycarbonylamino(4-amidinophenyl)methanephosphonate hydrochloride was dissolved in 150 ml of 2N HCl methanol solution and after addition of 5% Pd/C catalyst, the solution was stirred under an atmosphere of hydrogen until the theoretical amount of hydrogen was consumed. The catalyst was removed by filtration and after evaporation of the methanol, the residue was crystallized from ethanol-ether. In several experiments, the yields were 60-80%; mp. 213°-215° C.; Anal. Calcd. for C20 H22N3ClP.1/2 H2O: C,51.85; H, 4.97; N, 9.08; Cl, 15.34. Found: C, 51.73; H, 5.02; N, 9.10; Cl, 15.36.

Workup

  1. customwas consumed
  2. customThe catalyst was removed by filtration
  3. customafter evaporation of the methanol
  4. customthe residue was crystallized from ethanol-ether

Sources & evidence

ORD record
ord-d209ddd388bb4409bb653c98bdc5cb85
Source dataset
uspto-grants-1997_11
Patent number
US05686419

Reaction notes

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