4-Nitrophenol → 10-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid p-nitrophenyl ester

HRID 1164384Notes

Reaction equation

HRID 1164384 reaction equation
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([O:10][CH3:11])[CH:5]=[C:4]([CH3:12])[C:3]=1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23].[CH:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[C:27](O)[CH:26]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(#N)C>[N+:31]([C:30]1[CH:25]=[CH:26][C:27]([O:23][C:22](=[O:24])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:3]2[C:4]([CH3:12])=[CH:5][C:6]([O:10][CH3:11])=[C:7]([O:8][CH3:9])[C:2]=2[OH:1])=[CH:28][CH:29]=1)([O-:33])=[O:32]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 1290613810-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid

Product 1

HCID 5403291710-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid p-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10-(2-Hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid (236.9 mg, 0.7 mmol) and p-nitrophenol (107.1 mg, 0.77 mmol) were dissolved in acetonitrile (2 ml). To this solution was added DCC (158.9 mg, 0.77 mmol) under ice-cooling. The solution was stirred at room temperature for 16 hours. The insoluble material was removed by filtration and the solvent was evaporated under reduced pressure. The residue was chromatographed on a silica gel column with chloroform as eluent to obtain about 5 m mol of 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoic acid p-nitrophenyl ester. The ester was dissolved in DMF (1.5 ml). To this solution was added methyl 1-α-O-benzyl-N-acetylmuramyl-L-valyl-D-isoglutaminate (0.15 g, 0.25 mmol), HoBt(0.14 g, 1 mmol) and NEM (128 μl, 1 mmol) and the reaction mixture was stirred at room temperature for four days. After evaporation, the residue was purified by the chromatography on a silica gel column with chloroform/acetone/methanol (10:3:1, v/v) as eluent and precipitated as a gel from ethanol/ether to obtain methyl 1-α-O-benzyl-6-O-{10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoyl}-N-acetylmuramyl-L-valyl-D-isoglutaminate (0.13 g). [α]D22 +71.8° (C 0.5, DMF). Rf4 =0.70.

Workup

  1. temperaturecooling
  2. customThe insoluble material was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was chromatographed on a silica gel column with chloroform as eluent

Sources & evidence

ORD record
ord-8d9cd3aa5f2f491a856b092055a05ea7
Source dataset
uspto-grants-1983_01
Patent number
US04369178

Reaction notes

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