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Sodium Bicarbonate → Methyl 2-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzoate

HRID 602141
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HRID 602141 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:14][O:15][CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[CH:25]=[O:26])[CH2:18]3)=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[Na].[C:32](=O)(O)[O-:33].[Na+]>CO.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH2:14][O:15][CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23]4[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=4[C:25]([O:33][CH3:32])=[O:26])[CH2:18]3)=[C:11]([CH3:13])[N:12]=2)=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 575722032-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzaldehyde

생성물 1

HCID 58992617Methyl 2-[3-[[2-(4-chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzoate수율 58%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물
촉매
HCID 887Methanol용매

실험 절차

2-[3-[[2-(4-Chlorophenyl)-4-methylthiazol-5-yl]methoxymethyl]piperidin-1-yl]benzaldehyde (45.2 mg, 0.102 mmol) was dissolved in methanol (5 mL). To this solution, sodium cyamide (25.8 mg, 0.510 mmol) and manganese dioxide (88.7 mg, 1.02 mmol) were added and the mixture was stirred at room temperature for 3 hours. Subsequently, a saturated aqueous sodium bicarbonate solution was added and the mixture was filtered through Celite. The filtrate was extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the resulting residue by silica gel column chromatography (Chromatorex NH-DM2035, Fuji Silysia Chemical Co., Ltd.) (hexane:ethyl acetate=50:1->10:1) gave 27.9 mg (58%) of the desired compound as a colorless oil.

후처리

  1. filtrationthe mixture was filtered through Celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washthe extract washed with brine
  4. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  5. customPurification of the resulting residue by silica gel column chromatography (Chromatorex NH-DM2035, Fuji Silysia Chemical Co., Ltd.) (hexane:ethyl acetate=50:1->10:1)

출처 및 근거

ORD 기록
ord-6fe77a2daf7843288a06f238463ce96b
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07902367B2

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