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Toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl ester → 3-{4-[2-(1-Benzyl-3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-(2-fluoro-phenoxy)-2-methyl-propionic acid

HRID 1985138
ノート
印刷プレビュー

反応式

HRID 1985138 の反応式
C(=O)([O-])[O-].[Cs+].C([O:8][C:9](=[O:46])[C:10]([O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[F:45])([CH3:37])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH:21]2[CH2:25][N:24]([CH2:26][C:27]3[CH:32]=[CH:31][C:30](OC)=[CH:29][CH:28]=3)[C:23](=[O:35])[N:22]2[CH3:36])=[CH:14][CH:13]=1)C.[Cs+].C(OC(=O)C(OC1C=CC=CC=1F)(C)CC1C=CC(O)=CC=1)C.COC1C=CC(CN2CC(CCOS(C3C=CC(C)=CC=3)(=O)=O)N(C)C2=O)=CC=1>CN(C=O)C.C(OCC)(=O)C>[CH2:26]([N:24]1[CH2:25][CH:21]([CH2:20][CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([CH2:11][C:10]([O:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[F:45])([CH3:37])[C:9]([OH:46])=[O:8])=[CH:13][CH:14]=2)[N:22]([CH3:36])[C:23]1=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 57719164Toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl esterHCID 577192632-(2-Fluorophenoxy)-3-(4-hydroxyphenyl)-2-methyl-propionic acid ethyl esterHCID 867608772-(2-Fluoro-phenoxy)-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester Cesium carbonate

生成物 1

HCID 10289196
3-{4-[2-(1-Benzyl-3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-(2-fluoro-phenoxy)-2-methyl-propionic acid
収率 35,777,556%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-(2-Fluoro-phenoxy)-3-(4-{2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-methyl-propionic acid ethyl ester Cesium carbonate (6.12 g, 18.76 nmol) is added to a solution of 2-(2-Fluoro-phenoxy)-3-(4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester 1.99 g, 6.26 mmol) and toluene-4-sulfonic acid 2-[1-(4-methoxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethyl ester (2.88 g, 6.88 mmol) in DMF (20 mL). The resultant mixture is stirred at 65° C. under an atmosphere of nitrogen for 18 h, then diluted with ethyl acetate. The organic layer is washed with 1N HCl, water, and brine. The organic layer is dried over MgSO4, concentrated in vacuo, and purified by flash column chromatography (17% acetone in hexanes) to provide the title compound (3.4 g, 97%). 1H NMR (400 MHz, CDCl3): δ 7.19 (d, 2H, J=5.4 Hz), 7.17 (d, 2H, J=5.4 Hz), 7.07-7.01 (m, 1H), 6.97-6.87 (m, 3H), 6.83 (d, 2H, J=8.6 Hz), 6.74 (d, 2H, J=8.6 Hz), 4.32, 4.28 (ABq, 2H, J=14.6 Hz), 4.20 (q, 2H, J=7.5 Hz), 3.94 (t, 2H, J=5.9 Hz), 3.77 (s, 3H), 3.60-3.53 (m, 1H), 3.33 (t, 1H, J=8.6 Hz), 3.26, 3.14 (ABq, 2H, J=14.0 Hz), 2.92 (t, 1 h, J=8.6 Hz), 2.82 (s, 3H), 2.24-2.17 (m, 1H), 1.89-1.82 (m, 1H), 1.38 (s, 3H), 1.23 (t, 3H, J=7.5 Hz). MS [EI+] 565 (M+H)+. Rf=0.48 in 50% acetone in hexanes.

後処理

  1. washThe organic layer is washed with 1N HCl, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash column chromatography (17% acetone in hexanes)

出典と根拠

ORDレコード
ord-f18f7379543c4b06b0b9f8a424d2ef2a
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07544812B2

反応ノート

読み込み中…

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