Benzenesulfonyl chloride → HCID 67142036, compound

HRID 1864442Notes

Reaction equation

HRID 1864442 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=3[CH3:31])[CH2:20][CH2:19]2)=[O:17])[CH2:14][NH:13][C:12]1=[O:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[C:42]1([S:48](Cl)(=[O:50])=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C([O-])(O)=O.[Na+]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=3[CH3:31])[CH2:20][CH2:19]2)=[O:17])[CH2:14][N:13]([S:48]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)(=[O:50])=[O:49])[C:12]1=[O:32])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 67141134HCID 67141134, compound

Product 1

HCID 67142036HCID 67142036, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-2-oxo-imidazolidine-1-carboxylic acid benzyl ester (1.0 g), N-ethyl-diisopropylamine (0.43 mL) and 4-dimethylaminopyridine (0.14 g) in dichloromethane (15 mL) was added benzenesulfonyl chloride (0.35 mL) at 0° C. The mixture was stirred at ambient temperature for 3 h, a diluted aqueous solution of NaHCO3 was added, the phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried (Na2SO4), filtered and evaporated. The crude product was purified by column chromatography (SiO2, dichloromethane/methanol 98:2) to yield (S)-3-benzenesulfonyl-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-2-oxo-imidazolidine-1-carboxylic acid benzyl ester (1.08 g) as a white solid. MS: 576.8, ([M+H]+)

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by column chromatography (SiO2, dichloromethane/methanol 98:2)

Sources & evidence

ORD record
ord-152f69dfc0a44dcd8a1938d2bb93aa59
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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