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 2103450Notes

Reaction equation

HRID 2103450 reaction equation
[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

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

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);

Workup

  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)

Sources & evidence

ORD record
ord-9860661aed9e42ddbedf94fd2db0bee5
Source dataset
uspto-grants-2009_08
Patent number
US07576111B2

Reaction notes

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