Triethylamine → n-[2-(4-Methyl-2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester

HRID 1794934ノート

反応式

HRID 1794934 の反応式
Cl.Cl.[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH2:11])[CH3:4].C(N(CC)CC)C.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[C:23]([N+:31]([O-:33])=[O:32])[CH:22]=1>ClCCl>[CH2:3]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][C:23]=1[N+:31]([O-:33])=[O:32])(=[O:28])=[O:29])[CH3:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1046892-Nitro-p-toluenesulphonyl chlorideHCID 74889816N-beta-Aminoethyl-gly-oet 2hcl

生成物 1

HCID 22222384n-[2-(4-Methyl-2-nitro-benzenesulfonylamino)-ethyl]-glycine ethyl ester収率 92.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N-(2-aminoethyl)-glycine ethyl ester 2HCl (1.10 g, 5.0 mmol), prepared as described by Will (D. W. Will et al., Tetrahedron, 1995, 51, 12069–12802.), in dichloromethane (50 mL) was slowly added triethylamine (2.02 g, 20 mmol) at room temperature. Then 4-methyl-2-nitro-benzenesulfonyl chloride (1.19 g 5.0 mmol) in dichloromethane (10 mL) was added to the reaction mixture at room temperature for 5 min. The resulting reaction mixture was stirred for additional 2 h. at room temperature and washed with water (30 mL). The organic layer was dried over MgSO4 and filtered. The filtrate was evaporated in vacuo to give desired product (1.60 g, 92%) as a solid. 1H-NMR (500 MHz; DMSO-d6) δ 7.87 (d, 1H), 7.81 (s, 1H), 7.66 (d, 1H), 4.06 (q, 2H), 3.24 (s, 2H), 2.91 (t, 2H), 2.57 (t, 2H), 2.44 (s, 3H), 1.17 (t, 3H).

後処理

  1. customat room temperature
  2. customThe resulting reaction mixture
  3. washwashed with water (30 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

出典と根拠

ORDレコード
ord-197102b53369420e9412261001138352
出典データセット
uspto-grants-2006_04
特許番号
US07022851B2

反応ノート

読み込み中…