4-Nitrophenol → HCID 70154943, compound

HRID 2299026Notes

Reaction equation

HRID 2299026 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]=[CH:9]1.[N+:27]([C:30]1[CH:35]=[CH:34][C:33](O)=[CH:32][CH:31]=1)([O-:29])=[O:28].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13]([O:15][C:33]2[CH:34]=[CH:35][C:30]([N+:27]([O-:29])=[O:28])=[CH:31][CH:32]=2)=[O:14])[N:10]=[CH:9]1

Participants

7

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 57016800HCID 57016800, compound

Product 1

HCID 70154943HCID 70154943, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-[(5S)-3-(3-Fluoro-4-(4-carboxyimidazol-1-y l)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide (181 mg, 0.5 mM), 4-nitrophenol (139 mg, 1 mM), dicyclohexylcarbodiimide (144 mg, 0.7 mM) and 4-dimethylaminopyridine (61 mg, 0.5 mM) were dissolved in N,N-dimethylformamide (2 ml). The mixture was stirred at ambient temperature for 17 hours, diluted with dichloromethane (20 ml), washed with 1M aqueous sodium dihydrogen phosphate (10 ml), water (2×10 ml), and dried over magnesium sulfate. After filtration and evaporation to a suitable volume, the solution was chromatographed on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give title product (210 mg).

Workup

  1. washwashed with 1M aqueous sodium dihydrogen phosphate (10 ml), water (2×10 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration and evaporation to a suitable volume
  4. customthe solution was chromatographed on a 10 g silica Mega Bond Elut® column
  5. washeluting with
  6. temperaturea gradient increasing in polarity from 0 to 10% methanol in dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-d5d8559f1ca24c29ac919d0d50b8867b
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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