Methyl 2-(3,4-dichlorophenyl)acetate → HCID 67540431, compound

HRID 1192451Notes

Reaction equation

HRID 1192451 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.[C:14]([O:18][C:19]([N:21]1[CH:25]=[C:24]([CH2:26]Br)[N:23]=[CH:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:19]([N:21]1[CH:25]=[C:24]([CH2:26][CH:4]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=2)[C:3]([O:2][CH3:1])=[O:13])[N:23]=[CH:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 1268257Methyl 2-(3,4-dichlorophenyl)acetateHCID 67540258HCID 67540258, compound

Product 1

HCID 67540431HCID 67540431, compound

Procedure

4-[2-(3,4-Dichlorophenyl)-2-methoxycarbonyl-ethyl]-imidazole-1-carboxylic acid tert-butyl ester was prepared by the procedures described in Example 78, Step 1, substituting 3-tert-butoxycarbonylamino-propionic acid tert-butyl ester with (3,4-Dichlorophenyl)-acetic acid methyl ester and substituting 4-Bromo-1-bromomethyl-2-fluoro-benzene with 4-Bromomethyl-imidazole-1-carboxylic acid tert-butyl ester (prepared from 4(5)-hydroxymethylimidazole hydrochloride according to the literature: J. Med. Chem. 1997, 40, 2208). 1H NMR (CDCl3, 400 MHz) δ 7.96 (s, 1H), 7.42 (s, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.16 (d, J=8.0 Hz, 1H), 7.02 (s, 1H), 4.08 (t, J=7.6 Hz, 1H), 3.66 (s, 3H), 3.32 (dd, J=14.4 Hz, J=8.4 Hz, 1H), 2.92 (dd, J=14.4 Hz, J=6.8 Hz, 1H). LCMS (APCI+) m/z 299, 301, 303 [M-Boc+H]+; Rt=3.72 min.

Sources & evidence

ORD record
ord-3cee0339db2b4e6c83e333a888afaef0
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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