Potassium hydroxy sulfite → HCID 59676094, compound

HRID 642782Notes

Reaction equation

HRID 642782 reaction equation
[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15]1[C:14]3[CH:21]=[CH:22][CH:23]=[CH:24][C:13]=3[S:12][CH2:11][C:10]2=1)([CH3:4])([CH3:3])[CH3:2].[OH:27][O:28][S:29]([O-:31])=O.[K+]>CO.O.C1COCC1>[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[C:15]1[C:14]3[CH:21]=[CH:22][CH:23]=[CH:24][C:13]=3[S:12](=[O:27])[CH2:11][C:10]2=1)([CH3:4])([CH3:3])[CH3:2].[C:1]([Si:5]([CH3:26])([CH3:25])[O:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]1[C:14]3[CH:21]=[CH:22][CH:23]=[CH:24][C:13]=3[S:29](=[O:31])(=[O:28])[CH2:11][C:10]2=1)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 59676139HCID 59676139, compound

Product 2

HCID 59676094HCID 59676094, compoundHCID 59676101HCID 59676101, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 8-(tert-Butyl-dimethyl-silanyloxy)-11-methyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene (490 mg, 1.286 mmol), as prepared in Example 45, and OXONE (791 mg, 1.286 mmol) in MeOH (2 mL), H2O (2 mL) and THF (2 mL) was stirred at 25° C. After the solvent was removed in vacuo, the residue was partitioned between saturated NaHCO3 aqueous solution and CH2Cl2, the aqueous layer was extracted with CH2Cl2 and the organic layers were dried and concentrated to yield crude product. The crude product was purified by chromatography to yield 8-(tert-butyl-dimethyl-silanyloxy)-11-methyl-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene 5-oxide as a white solid, 11-methyl-5-oxo-6,11-dihydro-5H-5,4-thia-11-aza-benzo[a]fluoren-8-ol as a pale solid, and 8-(tert-butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene 5,5-dioxide as a white solid respectively.

Workup

  1. customAfter the solvent was removed in vacuo
  2. customthe residue was partitioned between saturated NaHCO3 aqueous solution and CH2Cl2
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. customthe organic layers were dried
  5. concentrationconcentrated
  6. customto yield crude product
  7. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-d7549bad8a874630a68c6701d5333516
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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