Benzenesulfonyl chloride → HCID 70181984, compound

HRID 726429Notes

Reaction equation

HRID 726429 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([NH2:29])[CH2:5][NH:6][C:7](=[O:28])[CH2:8][CH2:9][NH:10][C:11](=[O:27])[CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C(N(CC)CC)C.[C:38]1([S:44](Cl)(=[O:46])=[O:45])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>ClCCl>[CH3:1][O:2][C:3](=[O:30])[C@@H:4]([NH:29][S:44]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:46])=[O:45])[CH2:5][NH:6][C:7](=[O:28])[CH2:8][CH2:9][NH:10][C:11](=[O:27])[CH2:12][CH2:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 70181628HCID 70181628, compound

Product 1

HCID 70181984HCID 70181984, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound (120 mg) obtained in the above (5) is dissolved in dichloromethane (3 ml), and thereto are added triethylamine (98 μl) and benzenesulfonyl chloride (54 μl) at room temperature, and the mixture is stirred for 30 minutes. Triethylamine (98 μl) and benzenesulfonyl chloride (81 μl) are further added, and the mixture is stirred for 90 minutes. The mixture is evaporated under reduced pressure to remove the solvent, and to the residue is added ethyl acetate. The mixture is washed successively with 1N hydrochloric acid (twice), a saturated brine (once), a saturated aqueous sodium hydrogen carbonate solution (twice) and a saturated brine (twice), and dried over anhydrous magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (silica gel; 20 g, solvent; chloroform-methanol=30:1 to 10:1). The fractions containing the title compound are concentrated under reduced pressure to give the title compound (151 mg).

Workup

  1. stirringthe mixture is stirred for 90 minutes
  2. customThe mixture is evaporated under reduced pressure
  3. customto remove the solvent
  4. additionto the residue is added ethyl acetate
  5. washThe mixture is washed successively with 1N hydrochloric acid (twice), a saturated brine (once), a saturated aqueous sodium hydrogen carbonate solution (twice) and a saturated brine (twice), and
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe desiccant is removed by filtration
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography (silica gel; 20 g, solvent; chloroform-methanol=30:1 to 10:1)
  10. additionThe fractions containing the title compound
  11. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-5003b66ef247479882f5494115085198
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

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