4-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acid → dimethyl 4-[1-[4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]isophthalate

HRID 350341ノート

反応式

HRID 350341 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:21])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[CH2:27][O:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=1[C:39]([O:41][CH3:42])=[O:40]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:21])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:18]([N:22]2[CH2:26][CH2:25][CH2:24][CH:23]2[CH2:27][O:28][C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=2[C:39]([O:41][CH3:42])=[O:40])=[O:20])=[CH:15][CH:16]=1

参加物

5

反応物 2

HCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acidHCID 86595072dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalate

生成物 1

HCID 69333346dimethyl 4-[1-[4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]isophthalate収率 55%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of pentafluorophenyl ester of 4-[N′-(2-methylphenyl)ureido]phenylacetic acid (2.32 g, 5.15 mmol), dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalate (1.51 g, 5.15 mmol) in DMF (20 mL) was added Et3 N (1.0 mL, 6.65 mmol), and the mixture was stirred overnight. The resulting mixture was diluted with EtOAc. The solution was washed with brine, dried over MgSO4, and evaporated off in vacuo. The residue was purified by column chromatography on silica-gel with CHCl3-MeOH (10:1, v/v) as eluent to give 1.58 g (55%) dimethyl 4-[1-[4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]isophthalate as a yellow crystalline solid. 1H-NMR (CDCl3) δ 1.87–2.25 (m, total 7 H), 3.50–3.65 (m, 4 H), 3.85 (s, 3 H), 3.89 (s, 3 H), 4.18–4.31 (m, 2 H), 4.44 (m, 1 H), 6.95–8.45 (m, total 13 H).

後処理

  1. washThe solution was washed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated off in vacuo
  4. customThe residue was purified by column chromatography on silica-gel with CHCl3-MeOH (10:1

出典と根拠

ORDレコード
ord-8becd703227a46879486331ead9e672d
出典データセット
uspto-grants-2007_02
特許番号
US07179819B2

反応ノート

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