HCID 86722244, compound → HCID 178488264, compound

HRID 869400Notes

Reaction equation

HRID 869400 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]3[NH:9][CH:10]([C:16]4[N:17]=[C:18]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[S:19][CH:20]=4)[CH2:11][C:12](=[O:15])[C:13]=3[O:14][C:6]=2[CH:5]=[CH:4][C:3]=1[O:27][CH3:28]>C1COCC1.O=[Mn]=O>[OH:15][C:12]1[CH:11]=[C:10]([C:16]2[N:17]=[C:18]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[S:19][CH:20]=2)[N:9]=[C:8]2[C:7]3[C:2]([Cl:1])=[C:3]([O:27][CH3:28])[CH:4]=[CH:5][C:6]=3[O:14][C:13]=12

Participants

4

Reactant 1

HCID 86722244HCID 86722244, compound

Product 1

HCID 178488264HCID 178488264, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

11F (500 mg, 1.19 mmol) was dissolved in THF (tetrahydrofuran, 30 mL). To the solution was added activated MnO2 (600 mg, 6 eq, 6.9 mmol). The mixture was refluxed for 48 hours. After reaction completed, the mixture was cooled and filtered. The cake was washed well with THF and MeOH. The filtrate was concentrated and purified by column chromatography on silica gel to give 300 mg of pure product (11G).

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. customAfter reaction
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. washThe cake was washed well with THF and MeOH
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-04f9cea192bf4e1eb39e89784a8d9ef5
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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