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

HRID 333443노트

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HRID 333443 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 66987908HCID 66987908, 화합물HCID 178478688(1H-imidazol-4-yl)methanamine dihydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
80 °C

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-77901112944140f4815ffd680bf041ff
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877968B2

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