4-(2-Aminoethyl)benzenesulfonamide → HCID 46233761、化合物

HRID 1509776ノート

反応式

HRID 1509776 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH:14]([C:16]1[N:17]([CH2:21]C(OC(C)(C)C)=O)[CH:18]=[CH:19][N:20]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:43]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])(=[O:46])[CH:44]=O>ClCCCl.CC(O)=O>[CH3:21][N:17]1[CH:18]=[CH:19][N:20]=[C:16]1[CH2:14][N:1]([CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:10](=[O:11])(=[O:12])[NH2:13])=[CH:8][CH:9]=1)[CH2:44][C:43]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46]

参加物

7

反応物 4

HCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 5049666Sodium triacetoxyborohydrideHCID 10986247Tert-butyl 2-oxoacetateHCID 58291458tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate

生成物 1

HCID 46233761HCID 46233761、化合物収率 44.1%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

A solution of 4-(2-aminoethyl)benzenesulfonamide (0.70 g, 3.5 mmol), AcOH (0.20 mL) and tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.735 g, 3.5 mmol) in DCE (20 mL) was heated at 80° C. for 30 min under nitrogen. The reaction mixture was cooled to 0° C., and treated sequentially with NaBH(OAc)3 (2.25 g, 10.5 mmol) and tert-butyl glyoxalate (1.80 g). The reaction mixture was stirred at room temperature overnight and quenched with water. The reaction mixture was extracted with DCM and the organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford tert-butyl 2-(((1-methyl-1H-imidazol-2-yl)methyl)(4-sulfamoylphenethyl)amino)acetate (0.63 g, 35%). 1H NMR (400 MHz, DMSO-d6) δ 7.67 (d, J=8.4 Hz, 2H), 7.25 (s, 2H), 7.23 (d, J=8.4 Hz, 2H), 7.04 (d, J=1.2 Hz, 1H), 6.76 (d, J=1.2 Hz, 1H), 4.82 (s, 2H), 3.74 (s, 2H), 3.24 (s, 2H), 2.69-2.66 (m, 4H), 1.41 (s, 9H), 1.40 (s, 9H); ESMS m/z: 509 (M+H)+.

後処理

  1. customquenched with water
  2. extractionThe reaction mixture was extracted with DCM
  3. customthe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-923f23190ae6407c89cdc2d06b8fd668
出典データセット
uspto-grants-2012_07
特許番号
US08211402B2

反応ノート

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