4-Methylmorpholine → tert-Butyl 4-{4-[5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-3,5-dioxo-1-piperazinecarboxylate

HRID 499744ノート

反応式

HRID 499744 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][NH:14][C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:16])[O:10][C:9]2=[O:23])=[CH:4][CH:3]=1.[C:24](C(NCC(O)=O)C(O)=O)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C1C=CC2N(O)N=[N:46][C:44]=2[CH:45]=1.CN1CC[O:54][CH2:53][CH2:52]1.CN(C([O:64]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl.CN(C=O)C>[Cl:22][C:19]1[S:18][C:17]([C:15]([NH:14][CH2:13][CH:11]2[O:10][C:9](=[O:23])[N:8]([C:5]3[CH:6]=[CH:7][C:2]([N:1]4[C:45](=[O:64])[CH2:44][N:46]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:52][C:53]4=[O:54])=[CH:3][CH:4]=3)[CH2:12]2)=[O:16])=[CH:21][CH:20]=1

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21070787N-{[3-(4-aminophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}-5-chloro-2-thiophenecarboxamideHCID 56923762Boc-iminodi acetic acid

生成物 1

HCID 21070802tert-Butyl 4-{4-[5-({[(5-chloro-2-thienyl)carbonyl]amino}methyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}-3,5-dioxo-1-piperazinecarboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

300 mg (0.85 mmol) of N-{[3-(4-aminophenyl)-2-oxo-1,3-oxazolidin-5-yl]-methyl}-5-chloro-2-thiophenecarboxamide in 6 ml of a mixture of DMF and dichloromethane (1:1) are added to a solution of 199 mg (0.85 mmol) of Boc-iminodiacetic acid, 300 mg (2.2 mmol) of HOBT, 0.66 ml (6 mmol) of N-methylmorpholine and 647 mg (1.7 mmol) of HBTU. The mixture is stirred overnight before, after dilution with dichloromethane, being washed with water, saturated ammonium chloride solution, saturated sodium bicarbonate solution, water and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The crude product is purified by chromatography on silica gel (dichloromethane/methanol 98:2). Yield: 134 mg (29% of theory);

後処理

  1. washbeing washed with water, saturated ammonium chloride solution, saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product is purified by chromatography on silica gel (dichloromethane/methanol 98:2)

出典と根拠

ORDレコード
ord-b55b8c02e3714280b8247a1b9a195438
出典データセット
uspto-grants-2010_08
特許番号
US07767702B2

反応ノート

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