Water → 3-Iodo-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester
反応式
[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]参加物
実験手順
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.
後処理
- 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
出典と根拠
- ORDレコード
- ord-6db80506f29d40c6a919dc616dd41f40
- 出典データセット
- uspto-grants-2015_11
- 特許番号
- US09174976B2
反応ノート
読み込み中…