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

HRID 967462Notes

Reaction equation

HRID 967462 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-db2885f270d94c148533fb822cc55fbf
Source dataset
uspto-grants-2005_10
Patent number
US06953857B2

Reaction notes

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