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 734295노트

반응식

HRID 734295 반응식
[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

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

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);

후처리

  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)

출처 및 근거

ORD 기록
ord-532e9b4685bf489ba95228b14ea24130
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592339B2

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