Water → methyl(S)-2-[3-(1H-imidazol-4-ylmethyl)ureido]-3-(4-methoxy-phenyl)propanoate

HRID 333443ノート

反応式

HRID 333443 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH:15][C:16]([O:18]C2C=CC([N+]([O-])=O)=CC=2)=O)[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Cl.Cl.[NH:39]1[CH:43]=[C:42]([CH2:44][NH2:45])[N:41]=[CH:40]1.O>CN(C)C=O>[NH:39]1[CH:43]=[C:42]([CH2:44][NH:45][C:16](=[O:18])[NH:15][C@@H:10]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:11]([O:13][CH3:14])=[O:12])[N:41]=[CH:40]1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 66987908HCID 66987908、化合物HCID 178478688(1H-imidazol-4-yl)methanamine dihydrochloride

生成物 1

HCID 178501383methyl(S)-2-[3-(1H-imidazol-4-ylmethyl)ureido]-3-(4-methoxy-phenyl)propanoate収率 226.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

1.1 g (0.37 mmol) of methyl(S)-3-(4-methoxyphenyl)-2-(4-nitrophenoxycarbonyl-amino)propanoate (cf. preparation 2-2) and 0.7 mL (0.37 mmol) of diisopropyl-ethylamine in 5 mL of dimethylformamide are added at 80° C. to a solution of 500 mg (0.37 mmol) of C-(1H-imidazol-4-yl)methylamine dihydrochloride in 15 mL of dimethylformamide. The reaction mixture is stirred for 2 hours at 80° C. The reaction is stopped by adding 30 mL of water and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (eluent: 80/20 dichloromethane/methanol). 279 mg of methyl (S)-2-[3-(1H-imidazol-4-yl-methyl)-ureido]-3-(4-methoxyphenyl)propanoate in the form of a yellow oil are obtained in a yield of 63%.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (eluent: 80/20 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-77901112944140f4815ffd680bf041ff
出典データセット
uspto-grants-2014_11
特許番号
US08877968B2

反応ノート

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