Methanesulfonyl chloride → HCID 66991255, compound

HRID 454692Notes

Reaction equation

HRID 454692 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:35][C:15]=1[C:16]([NH:18][C:19]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl.N1C=CC=CC=1>[CH2:6]([O:13][C:14]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][N:42]2[CH2:47][CH2:46][N:45]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:44][CH2:43]2)=[CH:35][C:15]=1[C:16]([NH:18][C:19]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22])=[O:17])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 66990307HCID 66990307, compound

Product 1

HCID 66991255HCID 66991255, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, methanesulfonyl chloride (0.018 mL) was added to a solution mixture of methyl 2-(2-(benzyloxy)-5-(2-(piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate (0.11 g) in methylene chloride (2.2 mL) and pyridine (0.024 mL), followed by stirring at room temperature for 1 hour. Pyridine (0.016 mL) and methanesulfonyl chloride (9.0 μL) were sequentially added to the reaction mixture, followed by stirring at room temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 50-0% hexane/ethyl acetate] to obtain 0.085 g of methyl 2-(2-(benzyloxy)-5-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. stirringby stirring at room temperature for 1 hour and 30 minutes
  3. customThe solvent was evaporated under reduced pressure
  4. additiona saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 50-0% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-408d7661c14a4379b98206b0ced016c5
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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