Pyridine → HCID 16124726, compound

HRID 1945378Notes

Reaction equation

HRID 1945378 reaction equation
[C:1]12([C:11]3[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](O)=[O:18])=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(Cl)(=O)C(Cl)=O.[CH3:28][O:29][C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([NH2:38])[CH:32]=1.N1C=CC=CC=1>C1COCC1.CN(C=O)C>[CH3:28][O:29][C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([NH:38][C:17](=[O:18])[CH2:16][O:15][C:14]2[CH:13]=[CH:12][C:11]([C:1]34[CH2:10][CH:5]5[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]5)[CH2:8]3)[CH2:2]4)=[CH:21][CH:20]=2)[CH:32]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 65578Oxalyl chlorideHCID 625381PMID26882240-Compound-8

Product 1

HCID 16124726HCID 16124726, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(4-Adamantan-1-yl-phenoxy)-acetic acid (143.2 mg, 0.5-mmol) was dissolved in THF (5 mL), and oxalyl chloride (178.5 mg, 0.11 mL, 1.5 mmol) and one drop of DMF were added to the solution. After the mixture was stirred for 1 h at room temperature, 3-amino-4-hydroxy-benzoic acid methyl ester (125.4 mg, 0.75 mmol) and pyridine (0.05 mL) were added, and the resulting. Solution was stirred at room temperature overnight, and then partitioned between ethyl acetate and 10% HCl. The organic phase was washed with brine, dried (MgSO4-anh), and concentrated. The residue was purified by (n-Hexane:Ethyl acetate:MeOH=6:3:1) to give 3-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester as a white solid (183.2 mg, 84.1% yield).

Workup

  1. stirringSolution was stirred at room temperature overnight
  2. custompartitioned between ethyl acetate and 10% HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4-anh)
  5. concentrationconcentrated
  6. customThe residue was purified by (n-Hexane:Ethyl acetate:MeOH=6:3:1)

Sources & evidence

ORD record
ord-43de2799f4fa4fb9a798e55d8438b473
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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