Water → HCID 69879536, compound

HRID 352789Notes

Reaction equation

HRID 352789 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C@H:6]1[CH2:11][N:10]([S:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:25])[CH:21]=3)[CH:16]=2)(=[O:14])=[O:13])[CH2:9][C@H:8]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[NH:7]1)=[O:4].C(N(CC)C(C)C)(C)C.[Br:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](Cl)=[O:46])=[CH:43][CH:42]=1.O>ClCCl>[CH3:30][O:29][C:27]([CH2:26][C@H:8]1[CH2:9][N:10]([S:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([Cl:25])[CH:21]=3)[CH:16]=2)(=[O:13])=[O:14])[CH2:11][C@H:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[N:7]1[C:45](=[O:46])[C:44]1[CH:48]=[CH:49][C:41]([Br:40])=[CH:42][CH:43]=1)=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 69880819HCID 69880819, compound

Product 1

HCID 69879536HCID 69879536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (8 ml), the trans-2,6-bis(methoxycarbonylmethyl)-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine (79.7 mg) was dissolved. Under ice cooling, N,N-diisopropylethylamine (68.0 μl) and a solution of 4-bromobenzoyl chloride (51.0 mg) in dichloromethane (2 ml) were added to the resulting solution, followed by stirring at room temperature for 5.5 hours. Water was added to the reaction mixture to separate the organic layer. The organic layer was washed with saturate aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (n-hexane:ethyl acetate=l:1), whereby the title compound (113 mg, 98%) was obtained as pale yellow amorphous powder.

Workup

  1. customto separate the organic layer
  2. washThe organic layer was washed with saturate aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column (n-hexane:ethyl acetate=l:1), whereby the title compound (113 mg, 98%)
  7. customwas obtained as pale yellow amorphous powder

Sources & evidence

ORD record
ord-d3a141f5bdd54ca38b3577d75371cd7b
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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