4-(5-Ethoxycarbonylmethyl-2-methoxy-phenoxy)-3-isopropylsulfanylmethyl-benzoic acid methyl ester → 4-(5-Ethoxycarbonylmethyl-2-methoxy-phenoxy)-3-isopropylsulfanylmethyl-benzoic acid

HRID 656749Notes

Reaction equation

C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:14]=[CH:13][C:12]=2[O:23][CH3:24])=[C:6]([CH2:25][S:26][CH:27]([CH3:29])[CH3:28])[CH:5]=1>CN(C=O)C>[CH2:21]([O:20][C:18]([CH2:17][C:15]1[CH:14]=[CH:13][C:12]([O:23][CH3:24])=[C:11]([CH:16]=1)[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[CH:5][C:6]=1[CH2:25][S:26][CH:27]([CH3:28])[CH3:29])=[O:19])[CH3:22]

Participants

Conditions

Temperature: 65 °C

Procedure

4-(5-Ethoxycarbonylmethyl-2-methoxy-phenoxy)-3-isopropylsulfanylmethyl-benzoic acid methyl ester (0.5 g, 1.16 mmol) and sodium methylthiolate (0.16 g, 2.3 mmol) were combined in DMF (20 mL) and stirred at 65° C. for 1 hour. After an acidic work-up, the crude material was purified by preparative HPLC to give the title compound.

Workup

customAfter an acidic work-up, the crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-b52589ef02f8470bbf57ad3749845091
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071807B2

Reaction notes

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