Tetrahydrofuran → HCID 86750904, compound

HRID 1682774Notes

Reaction equation

HRID 1682774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:32][CH:33]=C)[CH:10]([C:21]2[N:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:24]=[N:23][CH:22]=2)[O:11][C:12](=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[O:35]1CCCC1.I([O-])(=O)(=O)=O.[Na+].ClCCl.C(OCC)(=O)C>C(OCC)C.O.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:32][CH:33]=[O:35])[CH:10]([C:21]2[N:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:24]=[N:23][CH:22]=2)[O:11][C:12](=[O:20])[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 21226138Dichloromethane ethylacetateHCID 23667635Sodium periodateHCID 69945394HCID 69945394, compound

Product 1

HCID 86750904HCID 86750904, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 5-[(1RS,2SR)-2-(3,4-dichlorophenyl)-1-phenylcarbamoyloxy-4-pentenyl]-1-phenyl-1,2,3-(1H)-triazole (1.0 g) in diethyl ether (4 mL), water (4 mL), and tetrahydrofuran (2 mL) was added a solution of 0.16M osmium tetroxide in water (0.22 mL). After 5 minutes sodium periodate (0.96 g) was added portionwise. After 2 hours at room temperature water was added to the reaction mixture until most of the solids dissolve. The mixture was extracted with ethyl acetate (2×50 mL); the combined organic layers dried, filtered, and the solvent evaporated to yield crude product as an oil. Chromatography, with dichloromethane:ethyl acetate (9:1) as the eluent gave the title compound 0.65 g (65%) as a white solid; NMR: 3.12 (d,2), 3.71-3.75 (m,1), 5.84 (d,1) 6.8 (dd,1), 7.03 (t,1), 7.17-7.57 (m,11), 8.01 (s,1), 9.54 (s,1); MS (CI, CH4): 495(M+1).

Workup

  1. dissolutiondissolve
  2. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
  3. customthe combined organic layers dried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customto yield crude product as an oil

Sources & evidence

ORD record
ord-7e43f1d3a8324a5e8ace31fa0ac8b85d
Source dataset
uspto-grants-1997_06
Patent number
US05635509

Reaction notes

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