Acetic Anhydride → HCID 66991398, compound

HRID 454689Notes

Reaction equation

HRID 454689 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH2:8]([O:15][C:16]1[CH:40]=[CH:39][C:38]([O:41][CH2:42][CH2:43][N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)=[CH:37][C:17]=1[C:18]([NH:20][C:21]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl.N1C=CC=CC=1>[C:1]([N:47]1[CH2:48][CH2:49][N:44]([CH2:43][CH2:42][O:41][C:38]2[CH:39]=[CH:40][C:16]([O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[C:17]([CH:37]=2)[C:18]([NH:20][C:21]2[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=[O:19])[CH2:45][CH2:46]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 66990307HCID 66990307, compound

Product 1

HCID 66991398HCID 66991398, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Under ice-cooling, acetic anhydride (0.025 mL) was added to a solution mixture of methyl 2-(2-(benzyloxy)-5-(2-(piperazin-1-yl)ethoxy)benzamido)-4-phenylbenzoate (0.12 g) in methylene chloride (2.4 mL) and pyridine (0.027 mL), followed by stirring at room temperature for 1 hour. 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: 100-95% chloroform/methanol] to obtain methyl 2-(5-(2-(4-acetylpiperazin-1-yl)ethoxy)-2-(benzyloxy)benzamido)-4-phenylbenzoate as a colorless oily substance.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under reduced pressure
  3. additiona saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-95% chloroform/methanol]

Sources & evidence

ORD record
ord-455a7c39a07941afbecfb4b48cc1fcd3
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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