Dimethylformamide → HCID 16124726, compound

HRID 1430774Notes

Reaction equation

HRID 1430774 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.CN(C=O)C.[CH3:33][O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([NH2:43])[CH:37]=1>C1COCC1.N1C=CC=CC=1>[CH3:33][O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([NH:43][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:37]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10815Methyl 3-amino-4-hydroxybenzoateHCID 65578Oxalyl chlorideHCID 625381PMID26882240-Compound-8

Product 1

HCID 16124726HCID 16124726, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Adamantan-1-yl-phenoxy acetic acid (143.2 mg, 0.5 mmol) was dissolved in 5 ml of THF and oxalyl chloride (178.5 mg, 0.11 ml, 1.5 mmol), to which DMF was added. After reacting the mixture at room temperature for 1 hour, 3-amino-4-hydroxy-benzoic acid methyl ester (125.4 mg, 0.75 mmol) and pyridine (0.05 ml) were added thereto. The reaction mixture was reacted at room temperature. Upon completion of the reaction, the reaction mixture was extracted with ethylacetate and NaCl solution, thereafter the organic layer was dried over anhydrous MgSO4, and concentrated. The residue was purified by silicagel column chromatography (N-Hexane: EtOAc:MeOH=6:3:1) to give the target compound as a white solid (183.2 mg, yield: 84.1%).

Workup

  1. customat room temperature
  2. customfor 1 hour
  3. customThe reaction mixture was reacted at room temperature
  4. customUpon completion of the reaction
  5. extractionthe reaction mixture was extracted with ethylacetate and NaCl solution
  6. dry with materialthe organic layer was dried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silicagel column chromatography (N-Hexane: EtOAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-87b65933e07c4629bb7cddb11737a229
Source dataset
uspto-grants-2015_01
Patent number
US08940936B2

Reaction notes

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