Water → HCID 86731294, compound

HRID 2277224Notes

Reaction equation

HRID 2277224 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH:24]1[CH2:26][CH2:25]1)[C:5]([NH:7][CH:8]1[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH:9]1[OH:18])=O.C(N(CC)CC)C.O>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:18][C:9]3[CH2:10][C:11]4([O:12][CH2:13][CH2:14][O:15]4)[CH2:16][CH2:17][C:8]=3[N:7]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH:24]1[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 86731293HCID 86731293, compound

Product 1

HCID 86731294HCID 86731294, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-chloro-4-(cyclopropylmethoxy)-N-(7-hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)benzamide (20.8 g) in dimethyl sulfoxide (80 mL) were added triethylamine (22.8 mL) and sulfur trioxide-pyridine complex (26.0 g), and the mixture was stirred for 1 hr under a nitrogen stream. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To a solution of the obtained residue in THF (80 mL) was added (methoxycarbonylsulfamoyl)triethylammonium hydroxide inner salt (21.4 g), and the mixture was stirred at 60° C. for 30 min. To the reaction mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (10.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionTo a solution of the obtained residue in THF (80 mL) was added (methoxycarbonylsulfamoyl)triethylammonium hydroxide inner salt (21.4 g)
  6. stirringthe mixture was stirred at 60° C. for 30 min
  7. additionTo the reaction mixture was added saturated brine
  8. extractionthe mixture was extracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated
  11. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7590bb7c8006470aaa12cf43cd3d7442
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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