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

HRID 454651
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HRID 454651 반응식
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
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매

3
HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

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온도
100 °C

실험 절차

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.

후처리

  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]

출처 및 근거

ORD 기록
ord-6ebe1304a662487fb127c7637590dbb0
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492582B2

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