Water → HCID 67126634, compound

HRID 1035959Notes

Reaction equation

HRID 1035959 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][OH:14])[CH2:8]2)OCC1.F[C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27].O>O1CCCC1>[N+:26]([C:17]1[CH:18]=[C:19]([S:22]([NH2:25])(=[O:23])=[O:24])[CH:20]=[CH:21][C:16]=1[O:14][CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][C:7](=[O:3])[CH2:8]1)([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 588050HCID 588050, compoundHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 67126634HCID 67126634, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 250 mL round-bottomed flask was added sodium hydride (0.5 g) in tetrahydrofuran (10 mL) and then 1,4-dioxaspiro[4.5]decan-7-ylmethanol (0.5 g) was added. After the mixture stirred at room temperature for 20 minutes, 4-fluoro-3-nitrobenzenesulfonamide (0.65 g) was added. The mixture was stirred at room temperature for overnight. Water (20 mL) was added slowly. The aqueous layer was extracted by dichloromethane (3×20 mL). The combined organic layers were dried over Na2SO4. After filtration, and concentration of the filtrate, the residue was purified by reverse phase chromatography, eluting with 30-60% acetonitrile in water with 0.1% trifluoroacetic acid.

Workup

  1. stirringThe mixture was stirred at room temperature for overnight
  2. extractionThe aqueous layer was extracted by dichloromethane (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationAfter filtration, and concentration of the filtrate
  5. customthe residue was purified by reverse phase chromatography
  6. washeluting with 30-60% acetonitrile in water with 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-521681875a37410986291f77859ca996
Source dataset
uspto-grants-2013_10
Patent number
US08546399B2

Reaction notes

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