Water → HCID 86607071, compound

HRID 2376662Notes

Reaction equation

HRID 2376662 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[C:6]([NH:14][C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH:5]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[N+:28]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1)([O-:30])=[O:29].O>CN(C=O)C.[Cl-].[Na+].O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:35][C:34]2[CH:37]=[CH:38][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=2)=[O:12])=[C:6]([NH:14][C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])[CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 23106772HCID 23106772, compound

Product 1

HCID 86607071HCID 86607071, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To (4-acetyl-2-{[(allyloxy)carbonyl]amino}phenyl)acetic acid (10.9 g) prepared by step g) and triethylamine (11 mL) in DMF (100 mL) was added at room temperature p-nitrobenzyl bromide (17.0 g), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added saturated brine (500 mL) and water (300 mL), and the mixture was extracted with ethyl acetate (200 mL, 2×100 mL). The organic layers were combined, washed with saturated brine (100 mL), dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The residue was purified with column chromatography (SiO2 300 g, hexane/ethyl acetate/chloroform=3:1:4˜0:1:1) to give the object compound (16.4 g, 98%) as a pale brown solid. Further the product was recrystallized from chloroform/hexane to give the object compound (10.4 g, 64%) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 mL, 2×100 mL)
  2. washwashed with saturated brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified with column chromatography (SiO2 300 g, hexane/ethyl acetate/chloroform=3:1:4˜0:1:1)

Sources & evidence

ORD record
ord-d1a1007ffce84de8b6eba843bb9cc8f6
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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