Methyl 3-hydroxy-4-methoxybenzoate → HCID 69652305, compound

HRID 1831797Notes

Reaction equation

HRID 1831797 reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([CH2:25]O)[CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.CCOC(/N=N/C(OCC)=O)=O>>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([CH2:25][O:12][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=3[O:10][CH3:11])[C:3]([OH:2])=[O:13])[CH2:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 5462977Diethyl azodicarboxylateHCID 13083368(1-(4-Chlorophenyl)cyclobutyl)methanol

Product 1

HCID 69652305HCID 69652305, compound

Procedure

To a solution of 300 mg 3-Hydroxy-4-methoxy-benzoic acid methyl ester, 388 mg [1-(4-Chloro-phenyl)-cyclobutyl]-methanol 1645 mg polymerbound triphenyl phosphine (Fluka, 3 mmol triphenyl phosphine/g resin) and 762 μl DEAD were introduced and the mixture was shaken over night at RT. After filtration, evaporation of the solvent the residue was taken up in 5 ml MeOH/H2O 3:1 and 20 mg LiOH monohydrate was added. After heating the mixture at 60° C. for 2 h the mixture was acidified with half concentrated HCl and filtered through a chem elut® cartridge by elution with ethyl acetate. After concentration under reduced pressure the crude product was subjected to the following amide coupling without further purification.

Workup

  1. filtrationAfter filtration, evaporation of the solvent the residue
  2. additionwas added
  3. temperatureAfter heating the mixture at 60° C. for 2 h the mixture
  4. filtrationfiltered through a chem elut® cartridge by elution with ethyl acetate
  5. concentrationAfter concentration under reduced pressure the crude product
  6. customwas subjected to the following amide coupling without further purification

Sources & evidence

ORD record
ord-a5cd6fe87b0844b09819f9c5a594951f
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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