Methyl iodide → 4-(3-Adamantan-1-yl-ureido)butyric Acid Methyl Ester

HRID 1444641ノート

反応式

HRID 1444641 の反応式
[C:1]12([NH:11][C:12](=[O:20])[NH:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:21]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[CH3:21][O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][NH:13][C:12]([NH:11][C:1]12[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2)=[O:20]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 114259954-(3-Adamantan-1-yl-ureido)butyric acid

生成物 1

HCID 114378554-(3-Adamantan-1-yl-ureido)butyric Acid Methyl Ester収率 95%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-(3-adamantan-1-yl-ureido)butyric acid 822 (0.15 g, 0.54 mmol), K2CO3 (0.09 g, 0.64 mmol), and iodomethane (0.04 mL, 0.59 mmol) in DMF (20 mL) was stirred at room temperature for 20 h. Then the product was extracted with ether (20 mL), and the ether was washed with 1 N NaOH aqueous solution (20 mL) and brine (20 mL), dried over Na2SO4, and evaporated to afford 0.15 g (95%) of 883: 1H NMR (CDCl3) 1.66-1.68 (6H, m), 1.81 (2H, quint, J=6.9 Hz), 1.94-1.97 (6H, m), 2.05-2.07 (3H, m), 2.37 (2H, t, J=6.9 Hz), 3.16 (2H, q, J=6.9 Hz), 3.68 (3H, s), 4.09 (1H, s), 4.25 (1H, s); LC-MS (ESI) m/z calcd for C16H26N2O3 [M+H]+ 295.19, found [M+H]+ 295.24; mp 114 C. Anal. (C16H26N2O3) C, H, N.

後処理

  1. extractionThen the product was extracted with ether (20 mL)
  2. washthe ether was washed with 1 N NaOH aqueous solution (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated

出典と根拠

ORDレコード
ord-f487971fe26b4ddbbaf9707aa1e824cc
出典データセット
uspto-grants-2010_02
特許番号
US07662910B2

反応ノート

読み込み中…