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 731580ノート

反応式

HRID 731580 の反応式
[C:1](C(NCC(O)=O)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=[N:23][C:21]=2[CH:22]=1.CN1CC[O:31][CH2:30][CH2:29]1.CN(C([O:41]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:58][C:59]1[CH:64]=[CH:63][C:62]([N:65]2[CH2:69][CH:68]([CH2:70][NH:71][C:72]([C:74]3[S:75][C:76]([Cl:79])=[CH:77][CH:78]=3)=[O:73])[O:67][C:66]2=[O:80])=[CH:61][CH:60]=1>ClCCl.CN(C=O)C>[Cl:79][C:76]1[S:75][C:74]([C:72]([NH:71][CH2:70][CH:68]2[O:67][C:66](=[O:80])[N:65]([C:62]3[CH:63]=[CH:64][C:59]([N:58]4[C:22](=[O:41])[CH2:21][N:23]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:29][C:30]4=[O:31])=[CH:60][CH:61]=3)[CH2:69]2)=[O:73])=[CH:78][CH:77]=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

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 is admixed with 300 mg (0.85 mmol) of N-{[3-(4-aminophenyl)-2-oxo-1,3-oxazolidin-5-yl]-methyl}-5-chloro-2-thiophene-carboxamide in 6 ml of a mixture of DMF and dichloromethane (1:1). The mixture is stirred overnight, diluted with dichloromethane and then washed with water, saturated ammonium chloride solution, saturated sodium bicarbonate solution, water and saturated sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated. The crude product is purified by silica gel chromatography (dichloromethane/methanol 98:2). Yield: 134 mg (29% of theory);

後処理

  1. washwashed 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 sulphate
  3. concentrationconcentrated
  4. customThe crude product is purified by silica gel chromatography (dichloromethane/methanol 98:2)

出典と根拠

ORDレコード
ord-bce75b758b9d492d9998733f473a7921
出典データセット
uspto-grants-2009_09
特許番号
US07585860B2

反応ノート

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