Water → methyl 4-[1-[4-[N'-(2-chlorophenyl)ureido]-3-methoxyphenyl acetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate

HRID 350504ノート

反応式

HRID 350504 の反応式
[C:1]1([C@@H:7]2[NH:11][C@H:10]([CH2:12][O:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32](=[O:46])[NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41](O)=[O:42])=[CH:36][C:35]=1[O:44][CH3:45].CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C>[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32](=[O:46])[NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41]([N:11]2[C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][C@H:10]2[CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=2)=[O:42])=[CH:36][C:35]=1[O:44][CH3:45]

参加物

6

反応物 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235118674-[N'-(2-chlorophenyl)ureido]-3-methoxyphenylacetic acidHCID 69332954methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate

生成物 1

HCID 20737840methyl 4-[1-[4-[N'-(2-chlorophenyl)ureido]-3-methoxyphenyl acetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzoate (142 mg, 0.46 mmol), 4-[N′-(2-chlorophenyl)ureido]-3-methoxyphenylacetic acid (153 mg, 0.46 mmol) and N,N-dimethylaminopyridine (55.7 mg, 0.46 mmol) in DMF (10 ml) was added EDC.HCl (95.7 mg, 0.50 mmol) at it, and the resulting mixture was stirred overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic layer was washed with brine, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (1:5) as eluent to give methyl 4-[1-[4-[N′-(2-chlorophenyl)ureido]-3-methoxyphenyl acetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (260 mg, 90%) as a colorless amorphous solid. 1H-NMR (CDCl3) δ 2.00–2.19 (m, 3 H), 2.35–2.44 (m, 1 H), 3.35 (s, 2 H), 3.76 (s, 3 H), 3.89 (s, 3 H), 4.38–4.48 (m, 2 H), 4.63 (br s, 1 H), 4.94 (t, J=7.2 Hz, 1 H), 6.53 (d, J=8.4 Hz, 1 H), 6.66 (s, 1 H), 6.96–7.01 (m, 3 H), 7.12–7.42 (series of m, 8 H), 7.87 (d, J=8.0 Hz, 1 H), 7.98 (d, J=8.8 Hz, 2 H), 8.17–8.19 (m, 1 H); MS (ESI) m/z, 627(+), 628 (M++H).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdrying over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel with hexane-EtOAc (1:5) as eluent

出典と根拠

ORDレコード
ord-fdca662891864dedb431a86b01c3e414
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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