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Potassium Carbonate → Tert-butyl 4-(2-(4-(benzyloxy)-3-(2-(methoxycarbonyl)-5-phenylphenylcarbamoyl)phenoxy)ethyl)piperidine-1-carboxylate

HRID 454685
Notes
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Reaction equation

HRID 454685 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].CN1CCCC1=O.[CH2:27]([O:34][C:35]1[CH:59]=[CH:58][C:57]([O:60][CH2:61][CH2:62]Br)=[CH:56][C:36]=1[C:37]([NH:39][C:40]1[CH:49]=[C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43])=[O:38])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(OCC)(=O)C.O>[CH2:27]([O:34][C:35]1[CH:59]=[CH:58][C:57]([O:60][CH2:61][CH2:62][CH:17]2[CH2:18][CH2:19][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])[CH2:15][CH2:16]2)=[CH:56][C:36]=1[C:37](=[O:38])[NH:39][C:40]1[CH:49]=[C:48]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:47]=[CH:46][C:41]=1[C:42]([O:44][CH3:45])=[O:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 7010304N-(tert-butoxycarbonyl)piperidineHCID 66990627Methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 66991035Tert-butyl 4-(2-(4-(benzyloxy)-3-(2-(methoxycarbonyl)-5-phenylphenylcarbamoyl)phenoxy)ethyl)piperidine-1-carboxylate
Yield 75.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Potassium carbonate (0.12 g) and 1-(tert-butoxycarbonyl)piperidine (0.15 g) were added to a 1-methyl-2-pyrrolidone (2.0 mL) solution of methyl 2-(2-(benzyloxy)-5-(2-bromoethoxy)benzamido)-4-phenylbenzoate (0.40 g), followed by stirring at 90° C. for 45 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. 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: 80-0% hexane/ethyl acetate] to obtain 0.36 g of tert-butyl 4-(2-(4-(benzyloxy)-3-(2-(methoxycarbonyl)-5-phenylphenylcarbamoyl)phenoxy)ethyl)piperidine-1-carboxylate as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 80-0% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-4fc052fd6d924739ac3a73dfe57b6996
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492582B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes