Methyl 3-(3,4-dimethoxyphenyl)propanoate → 2-Phenyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl-2-(3,4-dimethoxy-phenyl)methyl-2-propenoic Acid
Reaction equation
C1(C2NC(CO)=CN=2)C=CC=CC=1.[C:14]1([C:20]2[N:21]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[C:22]([CH2:25]O)=[CH:23][N:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(C1N(CC2C=CC=CC=2Cl)C(/C=C(\CC2C=CC3OCOC=3C=2)/C(OC)=O)=CN=1)CCC.C1(C2N(CC3C=CC=CC=3Cl)C(C=O)=CN=2)C=CC=CC=1.[CH3:89][O:90][C:91]1[CH:92]=[C:93]([CH2:99][CH2:100][C:101]([O:103]C)=[O:102])[CH:94]=[CH:95][C:96]=1[O:97][CH3:98]>[O-2].[O-2].[Mn+4]>[C:14]1([C:20]2[N:21]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[Cl:34])[C:22]([CH:25]=[C:100]([CH2:99][C:93]3[CH:94]=[CH:95][C:96]([O:97][CH3:98])=[C:91]([O:90][CH3:89])[CH:92]=3)[C:101]([OH:103])=[O:102])=[CH:23][N:24]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
7
Reactant 5
HCID 520347Methyl 3-(3,4-dimethoxyphenyl)propanoate
HCID 10080865(2-Phenyl-1H-imidazol-5-yl)methanol
HCID 10322320methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(3,4-methylenedioxyphenyl)methyl-2-propenoate
HCID 199368972-phenyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde
HCID 541028262-phenyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazoleProduct 1
Reagents, catalysts & solvents 1
Procedure
By the procedure of Example 1(ii) Method B, using benzamidine methyl ether in place of valeramidine methyl ether, 2-phenyl-5-hydroxymethylimidazole is prepared and converted to 2-phenyl-1-(2-chlorophenyl)methyl-5-hydroxymethyl-1H-imidazole. The 5-hydroxymethyl group is oxidized using manganese dioxide by the procedure of Example 1 (iii). The resulting 2-phenyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde is used in the procedure of Example 27 with methyl 3-(3,4-dimethoxyphenyl)propanoate to give the title compound.
Workup
- customis prepared
Sources & evidence
- ORD record
- ord-10b35f60b8cd48068fb7ddb4d428e2bd
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05312828
Reaction notes
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