HCID 18614890, compound → HCID 18614874, compound

HRID 1265168Notes

Reaction equation

HRID 1265168 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:24]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:23][C:22]([CH:34]=C)=[CH:21][C:20]=3[CH2:19]2)(=[O:16])=[O:15])=[CH:10][CH:9]=1>CC(O)(C)C.O1CCOCC1.O.ClCCl.[Os](=O)(=O)(=O)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:14]([NH:17][CH:18]2[CH2:27][CH2:26][C:25]3[C:24]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:23][C:22]([CH:34]=[O:2])=[CH:21][C:20]=3[CH2:19]2)(=[O:15])=[O:16])=[CH:12][CH:13]=1

Participants

8

Reactant 2

HCID 18614890HCID 18614890, compoundHCID 23667635Sodium periodate

Product 1

HCID 18614874HCID 18614874, compound

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2.5 g of a solution of osmium tetroxide (2.5% by weight) in 2-methyl-2-propanol, and then 20 g of sodium periodate, are added at ambient temperature to a solution of 10 g (23 mmol) of methyl 3-(6-{[(4-chlorophenyl)sulphonyl]amino}-3-vinyl-5,6,7,8-tetrahydro-1-naphth-yl)propanoate, described in Application EP 864 561, in a mixture of 100 ml of dioxan and 50 ml of water. After stirring for one night at ambient temperature, the solution is filtered and the filtrate is concentrated. The residue obtained is taken up in dichloromethane and washed with water, and the organic phase is dried and concentrated and then purified by chromatography on silica gel, using as eluant a cyclohexane/ethyl acetate mixture (60/40), to yield the expected compound.

Workup

  1. filtrationthe solution is filtered
  2. concentrationthe filtrate is concentrated
  3. customThe residue obtained
  4. washwashed with water
  5. customthe organic phase is dried
  6. concentrationconcentrated
  7. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-9e0f13a942844afab5e4e48ac089dc7a
Source dataset
uspto-grants-2003_04
Patent number
US06545037B2

Reaction notes

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