Potassium Iodide → Tert-butyl 2-(2-(benzyloxy)-5-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate

HRID 454651Notes

Reaction equation

HRID 454651 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[CH2:19]([O:26][C:27]1[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][C:28]=1[C:29]([NH:31][C:32]1[CH:44]=[C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:42]=[CH:41][C:33]=1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C.O.CN(C)C(=O)C>[CH2:19]([O:26][C:27]1[CH:54]=[CH:53][C:52]([O:55][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:51][C:28]=1[C:29]([NH:31][C:32]1[CH:44]=[C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:42]=[CH:41][C:33]=1[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 66990772Tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate

Product 1

HCID 66990330Tert-butyl 2-(2-(benzyloxy)-5-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoateYield 52.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (0.075 g), potassium iodide (0.090 g), and N-(2-chloroethyl)morpholine hydrochloride (0.041 g) were added to an N,N-dimethylacetamide (1.8 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate (0.090 g), followed by stirring at 100° C. for 1 hour. 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 bicarbonate, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 80-25% hexane/ethyl acetate] to obtain 0.058 g of tert-butyl 2-(2-(benzyloxy)-5-(2-(morpholin-4-yl)ethoxy)benzamido)-4-phenylbenzoate as a light yellow 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 bicarbonate
  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 [eluent: 80-25% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-6ebe1304a662487fb127c7637590dbb0
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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