Triphenylphosphine → HCID 66834513, compound

HRID 2275294Notes

Reaction equation

HRID 2275294 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[O:18])[C:16]3[C:15]4[C:10](=[CH:11][C:12]([S:19]([CH2:22][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)(=[O:21])=[O:20])=[CH:13][CH:14]=4)[NH:9][C:8]=3[C:7]([CH3:31])([CH3:30])[C:6]=2[CH:32]=1.[C:33]([SiH2]OC(C)(C)[C@@H]1OC(C)(C)O[C@@H]1CO)(C)([CH3:35])[CH3:34].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1COCC1.O.C(OCC)(=O)C>[CH:33]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[O:18])[C:16]3[C:15]4[C:10](=[CH:11][C:12]([S:19]([CH2:22][CH2:23][C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)(=[O:21])=[O:20])=[CH:13][CH:14]=4)[NH:9][C:8]=3[C:7]([CH3:30])([CH3:31])[C:6]=2[CH:32]=1)([CH3:35])[CH3:34]

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 5363146Diisopropyl azodicarboxylateHCID 66834837HCID 66834837, compoundHCID 131733422HCID 131733422, compound

Product 1

HCID 66834513HCID 66834513, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

8-Hydroxy-6,6-dimethyl-3-(2-phenyl-ethanesulfonyl)-5,6-dihydro-benzo[b]carbazol-11-one (30 mg, 0.0673 mmol), [(4R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]methanol (22.3 mg, 0.0808 mmol), and PPh3 (23 mg, 0.0875 mmol) were dissolved in THF (0.5 ml), added with DIAD (0.0169 ml, 0.0808 mmol), and the mixture was stirred at 50° C. overnight. After cooling, the reaction solution was filtered and concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane). The resulting residues were dissolved in THF (0.4 ml) and water (0.13 ml), added with camphor sulfonic acid (28.1 mg, 0.121 mmol), and then subjected to microwave irradiation at 80° C. for 15 min under nitrogen atmosphere. Ethyl acetate was added to the resultant. The organic layer was washed with saturated aqueous solution of sodium hydrocarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by thin layer chromatography (MeOH/DCM) to obtain Compound GT20-2 (10.5 mg) and Compound GT20-3 (2.4 mg).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction solution was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)
  5. dissolutionThe resulting residues were dissolved in THF (0.4 ml)
  6. customirradiation at 80° C. for 15 min under nitrogen atmosphere
  7. washThe organic layer was washed with saturated aqueous solution of sodium hydrocarbonate and saturated brine
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residues were purified by thin layer chromatography (MeOH/DCM)
  10. customto obtain Compound GT20-2 (10.5 mg) and Compound GT20-3 (2.4 mg)

Sources & evidence

ORD record
ord-c4fff691e7f843f6adbd8decee4ca924
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

Loading…