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Cesium fluoride → tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)phenoxy)piperidine-1-carboxylate

HRID 515270
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HRID 515270 반응식
[CH:1]1([CH2:4][NH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:7])[CH2:3][CH2:2]1.[F-].[Cs+].CS(O[CH:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]1)(=O)=O>CC(N(C)C)=O>[CH:1]1([CH2:4][NH:5][C:6](=[O:7])[NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[CH:13][CH:14]=2)[CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 25953Cesium fluorideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 671944861-(Cyclopropylmethyl)-3-(4-hydroxyphenyl)urea

생성물 1

HCID 67193130tert-Butyl 4-(4-(3-(cyclopropylmethyl)ureido)phenoxy)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

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온도
85 °C

실험 절차

To a stirring solution of 1-(cyclopropylmethyl)-3-(4-hydroxyphenyl)urea (6.79 mmol, 1.4 g) in dimethylacetamide (50 mL) was added cesium fluoride (20.36 mmol, 3.09 g) followed by a solution of tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (8.15 mmol, 2.276 g) in dimethylacetamide (50 mL). The resulting suspension was heated to 85° C. overnight. The reaction mixture was filtered and the filtrate concentrated under vacuum. The residue was dissolved in dichloromethane and washed with water. The organic layer was separated, dried over magnesium sulfate and concentrated under vacuum. The residue was dissolved in dichloromethane and purified by column chromatography (eluent 2-8% methanol in dichloromethane) to afford the title compound. MS (ESI) m/z 390.0 [M+H]+

후처리

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under vacuum
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. dissolutionThe residue was dissolved in dichloromethane
  9. custompurified by column chromatography (eluent 2-8% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-a2d857227f6549dea464a5b5fcdc6da7
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108939B2

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