Water → HCID 57035595, compound

HRID 1004510Notes

Reaction equation

HRID 1004510 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C@@H:5]([NH2:15])[CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:2].C(N(CC)CC)C.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>ClCCl>[CH2:1]([O:3][C:4](=[O:16])[C@@H:5]([NH:15][S:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:32])=[O:31])[CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 18665855HCID 18665855, compound

Product 1

HCID 57035595HCID 57035595, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained in the above (3) is dissolved in dichloromethane (15 ml), and thereto are added triethylamine (2.0 ml) and benzenesulfonyl chloride (1.57 ml) at room temperature, and the mixture is stirred for 30 minutes. To the mixture are further added triethylamine (0.57 ml) and benzenesulfonyl chloride (0.52 ml), and the mixture is further stirred for 30 minutes. The reaction mixture is poured into water, and the mixture is extracted three times with ethyl acetate. The extract 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; 100 g, solvent; hexane/ethyl acetate=1:1). The fractions containing the title compound are concentrated under reduced pressure to give the title compound (2.69 g) as a colorless powder.

Workup

  1. stirringthe mixture is further stirred for 30 minutes
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washThe extract 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
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant is removed by filtration
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (silica gel; 100 g, solvent; hexane/ethyl acetate=1:1)
  8. additionThe fractions containing the title compound
  9. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-df5e0b8fac76472f9698f5d223e9d87f
Source dataset
uspto-grants-2000_04
Patent number
US06048854

Reaction notes

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