Triethylamine → 4-(R)-benzyl-3(2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl)piperazine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one

HRID 393703ノート

反応式

HRID 393703 の反応式
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[N:30]1[C:35](=[O:45])[C@H:36]([CH2:40][S:41](Cl)(=[O:43])=[O:42])[CH:37]([CH3:39])[CH3:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl>[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[N:30]1[C:35](=[O:45])[C@H:36]([CH2:40][S:41]([N:19]1[CH2:20][CH2:21][N:16]([C:13]2[N:14]=[CH:15][C:10]([C:7]3[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=3)=[CH:11][N:12]=2)[CH2:17][CH2:18]1)(=[O:43])=[O:42])[CH:37]([CH3:39])[CH3:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 226466725-(4-Fluorophenyl)-2-piperazin-1-ylpyrimidine dihydrochlorideHCID 228882844-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3 methylbutyryl)oxazolidin-2-one

生成物 1

HCID 235197544-(R)-benzyl-3(2-(R)-{4-[5-(4-fluorophenyl)pyrimidin-2-yl)piperazine-1-sulfonylmethyl}-3-methylbutyryl)oxazolidin-2-one収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5-(4-Fluorophenyl)-2-piperazin-1-ylpyrimidine dihydrochloride (0.57 g) was added to a solution of 4-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3-methylbutyryl)-oxazolidin-2-one (0.77 g) in dichloromethane (20 ml) followed by triethylamine (0.84 ml), and the mixture stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure, and the residue dissolved in ethyl acetate (40 ml) and washed with 10% citric acid (2×20 ml), water (20 ml), saturated sodium bicarbonate solution (20 ml), water (20 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated. The resultant residue was then purified by silica gel column chromatography with 3.5% diethyl ether/dichloromethane as eluent to provide the title compound as a white solid (0.70 g, 69%).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (40 ml)
  3. washwashed with 10% citric acid (2×20 ml), water (20 ml), saturated sodium bicarbonate solution (20 ml), water (20 ml), saturated brine (20 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe resultant residue was then purified by silica gel column chromatography with 3.5% diethyl ether/dichloromethane as eluent

出典と根拠

ORDレコード
ord-29ba7606e61a4cb09a1c1fe021e8dddc
出典データセット
uspto-grants-2004_10
特許番号
US06809100B2

反応ノート

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