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Sulfuric acid magnesium salt (1:1) → tert-Butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indol-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710374
ノート
印刷プレビュー

反応式

HRID 710374 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][N:22]4[CH2:27][C:28]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[O:30][CH2:29]3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2]>ClCCCl.C(Cl)Cl.O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[CH:21][N:22]4[CH2:27][C:28]3([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:40])([CH3:42])[CH3:41])[CH2:29][O:30][C:31]([CH3:34])([CH3:35])[O:32][CH2:33]3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 66726782tert-Butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

生成物 1

HCID 86661784tert-Butyl 5-((4-(5-(3,4-diethoxyphenyl)-1,2,4-oxadiazol-3-yl)indol-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate収率 28.6%

試薬・触媒・溶媒 3

HCID 14801Manganese dioxide触媒
HCID 11
1,2-Dichloroethane
溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

A suspension of the product of Example 34, Step D (0.07 g; 0.118 mmol), MnO2 (0.58 g; 6.67 mmol) and anhydrous MgSO4 (0.5 g; 4.2 mmol) in 1,2-dichloroethane (2.5 ml) was vigorously stirred for 2 h at ˜50° C., then overnight at room temperature. This was diluted to 20 ml with CH2Cl2 and filtered through Celite pad, washed with fresh CH2Cl2 (10 ml). The combined organic phase was evaporated under reduced pressure and the residue was purified by FCC (SiO2, CH2Cl2/EtOAc 9:1) to give the title compound (0.02 g; 28%), as creamy solid. 1H-NMR (CDCl3) 1.43-1.53 (m, 21H+H2O); 3.78 (d, 2H, J=11.9 Hz); 3.90 (d, 2H, J=11.9 Hz); 4.13-4.38 (m, 5H); 4.76 (s, 1H); 6.98 (d, 1H, J=8.5 Hz); 7.15 (s, 1H); 7.28-7.34 (m, 2H); 7.68 (d, 1H, J=8.4 Hz); 7.73 (d, 1H, J=1.9 Hz); 7.83 (dd, 1H, J=1.9, 8.4 Hz); 8.03 (d, 1H, J=7.2 Hz).

後処理

  1. customovernight
  2. customat room temperature
  3. filtrationfiltered through Celite pad
  4. washwashed with fresh CH2Cl2 (10 ml)
  5. customThe combined organic phase was evaporated under reduced pressure
  6. customthe residue was purified by FCC (SiO2, CH2Cl2/EtOAc 9:1)

出典と根拠

ORDレコード
ord-78edccd3b57e440fb27da0e16c1c3902
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181182B2

反応ノート

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