Water → methyl 4-[1-[4-[N'-(2,6-dichlorophenyl)ureido]-3-methoxyphenylacetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate

HRID 350506노트

반응식

HRID 350506 반응식
[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]=[C:29](Cl)[CH:28]=[CH:27][C:26]=1[NH:32][C:33](=[O:47])[NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]([OH:44])=O)=[CH:37][C:36]=1[O:45][CH3:46].CCN=C=NCCCN(C)C.[ClH:59].O>CN(C=O)C>[Cl:59][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([Cl:24])[C:26]=1[NH:32][C:33](=[O:47])[NH:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]([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:44])=[CH:37][C:36]=1[O:45][CH3:46]

참가 물질

6

반응물 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23512519HCID 23512519, 화합물HCID 69332954methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzate

생성물 1

HCID 20737829methyl 4-[1-[4-[N'-(2,6-dichlorophenyl)ureido]-3-methoxyphenylacetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzoate (109 mg, 0.35 mmol), 4-[N′-(2,4-dichlorophenyl)ureido]-3-methoxyphenylacetic acid (129 mg, 0.35 mmol) and N,N-dimethylaminopyridine (42.8 mg, 0.35 mmol) in DMF (10 ml) was added EDC.HCl (73.4 mg, 0.39 mmol) at rt, and the resulting mixture was stirred for 6 h. 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 (1:4) as eluent to give methyl 4-[1-[4-[N′-(2,6-dichlorophenyl)ureido]-3-methoxyphenylacetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (208 mg, 90%) as a colorless amorphous solid. 1H-NMR (CDCl3) δ 2.00–2.21 (m, 3 H), 2.33–2.39 (m, 1 H), 3.31 (s, 2 H), 3.69 (s, 3 H), 3.88 (s, 3 H), 4.34–4.45 (m, 2 H), 4.59 (br s, 1 H), 4.93 (t, J=6.8 Hz, 1 H), 6.47 (d, J=8.0 Hz, 1 H), 6.63 (s, 1 H), 6.68 (s, 1 H), 6.92–6.95 (m, 2 H), 7.12–7.41 (series of m, 9 H), 7.96–8.01 (m, 4 H); MS (FAB) m/z, 662 (M++H).

후처리

  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 (1:4) as eluent

출처 및 근거

ORD 기록
ord-2ab4cb90afd74f00b2990da70560c320
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179819B2

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