Water → HCID 54332622, compound

HRID 1417487Notes

Reaction equation

HRID 1417487 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[C:18]([CH2:21][C:22](O)=[O:23])[CH:17]=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:31][S:32]([NH2:35])(=[O:34])=[O:33].O>C(Cl)Cl.C(Cl)(=O)C(Cl)=O>[CH3:31][S:32]([NH:35][C:22](=[O:23])[CH2:21][C:18]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:20]=2[CH:19]=1)(=[O:34])=[O:33]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 72879MethanesulfonamideHCID 53645035HCID 53645035, compound

Product 1

HCID 54332622HCID 54332622, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 65578Oxalyl chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.055 ml (0.63 nmol) of oxalyl chloride was added, with ice-cooling, to a mixture of 100 mg (0.32 mmol) of (9-benzylcarbazol-2-yl)acetic acid (prepared as described in Example 42) in 3 ml of methylene chloride, and the whole was stirred for 30 minutes at room temperature. After this time, the solvent was removed by evaporation under reduced pressure. 5 ml of methylene chloride, 0.08 ml (0.99 mmol) of pyridine and 60 mg (0.63 mmol) of methanesulfonamide were added to the residue thus obtained, with ice-cooling. The reaction mixture was then stirred for 12 hours at room temperature. After the reaction had been allowed to go to completion, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic fraction was then washed with water and dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography, using 30 g of silica gel with a 50% v/v solution of methanol in ethyl acetate as eluent, to yield 46 mg of the title compound as an amorphous solid.

Workup

  1. customAfter this time, the solvent was removed by evaporation under reduced pressure
  2. customthus obtained, with ice-
  3. temperaturecooling
  4. stirringThe reaction mixture was then stirred for 12 hours at room temperature
  5. additionwas added to the reaction mixture, which
  6. extractionwas then extracted with ethyl acetate
  7. washThe organic fraction was then washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed by evaporation under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4264a63514e4b99acfd47476e8bab48
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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