HCID 10430792, compound → HCID 10429934, compound

HRID 2181808Notes

Reaction equation

HRID 2181808 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH:27]([CH3:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5]>O1CCCC1>[OH:5][CH2:4][C:3]1[CH:7]=[C:8]([S:11]([N:14]2[CH:27]([CH3:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]2=3)(=[O:12])=[O:13])[CH:9]=[CH:10][C:2]=1[OH:1]

Participants

3

Reactant 1

HCID 10430792HCID 10430792, compound

Product 1

HCID 10429934HCID 10429934, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of crude 2-hydroxy-5-[(6-methylphenanthridin-5(6H)-yl)sulfonyl]benzoic acid (1.75 g, 4.43 mmol) in anhydrous tetrahydrofuran (20 mL) was treated drop-wise at room temperature under nitrogen via syringe with 10 M borane-methyl sulfide complex (1.5 mL, 15 mmol). After stirring four hours at room temperature, the reaction was quenched with methanol (20 mL), concentrated in vacuo, diluted with water, and extracted with ethyl acetate. The organic phase was washed sequentially with an aqueous solution of potassium carbonate, water, a saturated, aqueous, sodium chloride solution, a 1 N hydrochloric acid solution, and water. The organic phase was dried over anhydrous sodium sulfate, filtered through a short column of silica gel, and eluted with ethyl acetate. The ethyl acetate phase was evaporated in vacuo to a crude oil (1.2 g). The crude oil was purified by preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g) with gradient elution of between 10% to 55% methyl tert-butyl ether in hexane at a flow rate of 50 mL/min; and afforded, after evaporation of the solvent, a colorless oil (0.687 g. 1.8 mmol). Crystallization of the colorless oil from diethyl ether yielded the title compound (0.6 g, 1.57 mmol, 35%) as a homogeneous, colorless, crystalline, solid, m.p. 182-184° C.;

Workup

  1. customthe reaction was quenched with methanol (20 mL)
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed sequentially with an aqueous solution of potassium carbonate, water
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered through a short column of silica gel
  8. washeluted with ethyl acetate
  9. customThe ethyl acetate phase was evaporated in vacuo to a crude oil (1.2 g)
  10. customThe crude oil was purified by preparative chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g) with gradient elution of between 10% to 55% methyl tert-butyl ether in hexane at a flow rate of 50 mL/min
  11. customand afforded
  12. customafter evaporation of the solvent
  13. customCrystallization of the colorless oil from diethyl ether

Sources & evidence

ORD record
ord-35241f972c5c44d48b8991a945198844
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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