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 731580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731580
[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

Komponenten

8

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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);

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-bce75b758b9d492d9998733f473a7921
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585860B2

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