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

HRID 354480ノート

反応式

HRID 354480 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])=[O:11].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][NH:40][CH2:41][CH3:42])[C:29]([O:31][CH2:32][CH3:33])=[O:30].CCN(CC)CC>>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][CH2:39][NH:40][CH2:41][CH2:42][C:21](=[O:23])[CH2:20][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30]

参加物

4

反応物 3

HCID 8471TriethylamineHCID 23511825HCID 23511825、化合物HCID 23512488Ethyl 3-methoxy-4-(2-ethylaminoethoxy)benzoate

生成物 1

HCID 69333489ethyl 3-methoxy-4-[2-[3-methoxy-4-[N'-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate収率 100.7%

実験手順

To a stirred solution of pentafluorophenyl ester of 3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetic acid (135 mg, 0.28 mmol) and ethyl 3-methoxy-4-(2-ethylaminoethoxy)benzoate (78 mg, 0.29 mmol) was added Et3N (0.1 mL, 0.72 mmol), and the resulting mixture was stirred overnight. The mixture was diluted with EtoAc, washed successively with 0.5N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1, v/v) as eluent to give 160 mg (q.y.) ethyl 3-methoxy-4-[2-[3-methoxy-4-[N′-(2-fluorophenyl)ureido]phenylacetyl]ethylaminoethoxy]benzoate as an oil. 1H-NMR (CDCl3) d 1.13-1.23 (m, 3 H), 1.37-1.40 (m, 3 H), 2.90-3.89 (m, 12 H), 4.09-4.28 (m, 2 H), 4.33-4.39 (m, 2 H), 6.70-8.21 (series of m, total 12 H).

後処理

  1. additionThe mixture was diluted with EtoAc
  2. washwashed successively with 0.5N HCl, brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (50:1

出典と根拠

ORDレコード
ord-6a2fb41633694c28b1cffb1db3e1526c
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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