Water → 3-Iodo-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester
Reaction equation
[Na+].[I-:2].[C:3]([O-:6])([O-])=O.[K+].[K+].[CH3:9][O:10][C:11](=[O:24])[CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15].O.CN([CH:29]=[O:30])C>>[CH3:3][O:6][C:29](=[O:30])[C:19]1[CH:18]=[CH:17][CH:22]=[C:21]([I:2])[C:20]=1[CH2:23][N:13]([CH2:12][C:11]([O:10][CH3:9])=[O:24])[S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15]Participants
Procedure
A mixture of 3-iodo-2-methyl-benzoic acid methyl ester (75 mmol, 20.7 g), N-bromosuccinimide (76.6 mmol, 13.8 g), benzoyl peroxide (890 mg), and CCl4 (300 mL) was refluxed with stirring for 15 h. After cooling to ambient temperature the mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as a tan oil. The oil (26.3 g) was dissolved in dry DMF (75 mL). NaI (22.4 g), K2CO3 (20.5 g), and (toluene-4-sulfonylamino)-acetic acid methyl ester (19 g) were added and the mixture was stirred at ambient temperature for 24 h before it was poured into water (900 mL). The mixture was extracted with ethyl acetate (2×250 mL). The combined organic phases were washed with a solution of sodium meta-bisulfite (20 g) in water (300 mL) and water (2×300 mL) before they were dried over MgSO4 and concentrated in vacuo to give the title compound as a dark gum (38.1 g). The crude product was used in the next step without further purification; MS-(+)-ion: M+23=539.9.
Workup
- extractionThe mixture was extracted with ethyl acetate (2×250 mL)
- washThe combined organic phases were washed with a solution of sodium meta-bisulfite (20 g) in water (300 mL) and water (2×300 mL) before they
- dry with materialwere dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-70637a2524d440d7a993b0f63f744593
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759373B2
Reaction notes
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