3-hydroxy-1,2,3-benzotriazin-4(3H)-one → (4-Nitro-2-phenylbenzoyl)methionine methyl ester

4-Nitro-2-phenylbenzoic acid (50.0 g, 205 mmol) and 3-hydroxy1,2,3-benzotriazin-4(3H)-one (36.89 g, 226 mmol) were dissolved in 500 mL DMF. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (47.3 g, 247 mmol) and methionine methyl ester hydrochloride (53.37 g, 267 mmol) were added followed by triethylamine (31.5 mL, 226 mmol). Additional triethylamine was added to raise the pH to 6˜7. After 1 hour at ambient temperature, the reaction mixture was concentrated to 200 mL, diluted with 500 mL ethyl acetate, washed with 1 M HCl, 5% NaHCO3, and brine, and dried over Na2SO4 to provide (4-nitro-2-phenylbenzoyl)methionine methyl ester which was used directly without further purification. MS m/e 389 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.78 (m, 2H), 2.01 (s, 3H), 2.60 (m, 2H), 3.69 (s, 3H), 4.69 (m, 1H), 6.02 (d, J=8 Hz, 1H), 7.48,(m, 5H), 7.85 (m, 1H), 8.27 (m, 2H).

1. temperatureto raise the pH to 6˜7
2. concentrationthe reaction mixture was concentrated to 200 mL
3. additiondiluted with 500 mL ethyl acetate
4. washwashed with 1 M HCl, 5% NaHCO3, and brine
5. dry with materialdried over Na2SO4

ORDレコード

ord-0c42984f4720439badd03ff4c1a6c548

出典データセット

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06693123B2