Triethylamine → ethyl 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate

HRID 354475노트

반응식

HRID 354475 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][NH:17][CH2:18][CH3:19])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:39][C:40](O)=[O:41])[CH:25]=[CH:26][C:27]=1[NH:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH3:38])=[O:30].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:40](=[O:41])[CH2:39][C:24]1[CH:25]=[CH:26][C:27]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])=[O:30])=[C:22]([O:21][CH3:20])[CH:23]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23512488Ethyl 3-methoxy-4-(2-ethylaminoethoxy)benzoate

생성물 1

HCID 69332900ethyl 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate수율 93%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of ethyl 3-methoxy-4-(2-ethylaminoethoxy)benzoate (290 mg, 1.08 mmol) and pentafluorophenyl ester of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (502 mg, 1.05 mmol) in DMF (7 mL) was added Et3N (250 μl, 1.79 mmol), and the resulting mixture was stirred overnight. The mixture was diluted with EtOAc, washed with 0.5 N HCl, brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by column chromatography on silica-gel with CHCl3—MeOH (40:1, v/v) as an eluent to give 550 mg (93%) ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate as an amorphous solid. 1H-NMR (CDCl3) d 1.11-1.18 (m, 3 H), 1.37-1.41 (m, 3 H), 2.30 (s, 3 H), 3.47-3.53 (m, 2 H), 3.61-3.75 (m, 7 H), 3.84 (s, 3 H), 4.03-4.27 (m, 2 H), 4.33-4.39 (m, 2 H), 6.34-8.07 (series of m, total 12 H).

후처리

  1. washwashed with 0.5 N HCl, brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (40:1

출처 및 근거

ORD 기록
ord-b4f09340a11043eab3361b0f45bcc2bc
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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