HCID 15434401, compound → HCID 9889997, compound

HRID 1585476Notes

Reaction equation

HRID 1585476 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][P:26]([O:36]CC2C=CC=CC=2)([O:28]CC2C=CC=CC=2)=[O:27])=[C:6]([CH2:8][N:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[O:11][C:10]2=[O:24])[CH:7]=1>C(OCC)(=O)C.C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][P:26]([OH:28])([OH:36])=[O:27])=[C:6]([CH2:8][N:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=3)[O:11][C:10]2=[O:24])[CH:7]=1

Participants

5

Reactant 1

HCID 15434401HCID 15434401, compound

Product 1

HCID 9889997HCID 9889997, compoundYield 97.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a Parr hydrogenation flask containing 3.7 mg of 10% Pd/C was added a solution of 50 mg (0.080 mmol) of 3-[(5-chloro-2-[[bis[phenylmethyl]phosphono]oxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one dissolved in 2 mL of ethyl acetate and 5 mL of ethanol. The mixture was hydrogenated at 40 psi for 40 minutes, filtered through celite and the filtrate was concentrated to give 35 mg of 3-[(5-chloro-2-[phosphonooxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one as a white solid: m.p. 173-176° C. MS 449 (M--H)-.

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f99eb9bbdde44526bdcce18bc53b9b18
Source dataset
uspto-grants-1999_08
Patent number
US05939405

Reaction notes

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