Tetrahydrofuran → HCID 15434404, compound

HRID 1585478Notes

Reaction equation

HRID 1585478 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:26]([CH2:28][O:29][P:30]([O:40]CC2C=CC=CC=2)([O:32]CC2C=CC=CC=2)=[O:31])=[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.C1COCC1>C(OCC)(=O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][C:26]([CH2:28][O:29][P:30]([OH:32])([OH:40])=[O:31])=[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 2

HCID 8028TetrahydrofuranHCID 21218592HCID 21218592, compound

Product 1

HCID 15434404HCID 15434404, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[[5-chloro-2-[[[[bis-(phenylmethyl)phosphonooxy]methyl]carbonyl]oxy]phenyl]methyl]-5-[4-(trifluoromethyl)phenyl]- 1,3,4 -oxadiazol-2(3H)-one (138 mg, 0.20 mmol) in ethyl acetate (30 mL) and PtO2 (30 mg) was hydrogenated at 30 psi in a Parr apparatus for 1 hr. After hydrogenation is complete, THF (30 mL) was added to solublize the product and then filtered through a pad of Celite to remove the catalyst. The filtrate was evaporated and the residue was recrytallized twice from ether-hexanes and then acetone-hexanes to afford the title compound as a white powder (83 mg, 82%). MS m/e 509 (MH+).

Workup

  1. filtrationfiltered through a pad of Celite
  2. customto remove the catalyst
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c901092fb92340b3b16a61d45b173a81
Source dataset
uspto-grants-1999_08
Patent number
US05939405

Reaction notes

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