Methanol → 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3,4-dihydro-2H-chromene-4-carboxylic acid

HRID 1021482Notes

Reaction equation

HRID 1021482 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:31]=[CH:30][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([O:28]C)=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][CH:17]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.CO.[OH-].[Na+]>C1COCC1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:26]([OH:28])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][CH:17]=3)=[CH:30][CH:31]=2)=[O:10])=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67080596Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3,4-dihydro-2H-chromene-4-carboxylate

Product 1

HCID 670806047-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3,4-dihydro-2H-chromene-4-carboxylic acidYield 37.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3,4-dihydro-2H-chromene-4-carboxylate was dissolved in THF (3 mL) and methanol (3 mL) and treated with 1N NaOH (3 mL), and the reaction was stirred for 1 hour. The reaction was diluted with CH2Cl2 (25 mL) and washed with 2N HCl (25 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 0.5% MeOH/CH2Cl2 containing 0.5% acetic acid to 7.5% MeOH/CH2Cl2 containing 0.5% acetic acid to provide the title compound (0.056 g, 37.8% yield) as a white solid. MS (ESI)=452.1 (M+1).

Workup

  1. washwashed with 2N HCl (25 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 0.5% MeOH/CH2Cl2 containing 0.5% acetic acid to 7.5% MeOH/CH2Cl2 containing 0.5% acetic acid

Sources & evidence

ORD record
ord-b4d0d83f88ce4041b26aa446ba6579cf
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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