Triethylamine → 3-Allyl-4-oxo-1-pyridin-2-yl-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

HRID 1783428ノート

反応式

HRID 1783428 の反応式
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]([C@@H:11]2[C@@H:14]([CH2:15][CH:16]=[CH2:17])[C:13](=[O:18])[NH:12]2)=[O:10])=[CH:5][CH:4]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([CH:11]2[CH:14]([CH2:15][CH:16]=[CH2:17])[C:13](=[O:18])[N:12]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)=[O:10])=[CH:19][CH:20]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 2762745Pyridine-2-boronic acidHCID 57589773(2S,3R)-3-Allyl-4-oxo-azetidine-2-carboxylic acid 4-methoxy-benzyl ester

生成物 1

HCID 686039533-Allyl-4-oxo-1-pyridin-2-yl-azetidine-2-carboxylic acid 4-methoxy-benzyl ester収率 24.8%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of β-lactam 59 (60 mg, 0.22 mmol), Pyridin-2-boronic acid (81 mg, 0.66 mmol), copper acetate (120 mg, 0.66 mmol), triethylamine (0.153 mL, 1.1 mmol) and activated 4A molecular sieves (270 mg) in dichloromethane (5 mL) was stirred at room temperature for 2 days. The reaction mixture was filtered through celite and the filtrate was concentrated. Preparative TLC (20% EtOAc/Hexanes) of the residue gave the desired product 80 (19.2 mg, 24.8%) 1HNMR (300 MHz, CDCl3): 2.60 (m, 2H), 3.49 (m, 1H), 3.81 (s, 3H), 4.41 (d, J=2.61 Hz, 1H), 5.11-5.21 (m, 4H), 5.82 (m, 1H), 6.85 (d, J=8.7 Hz, 2H), 7.01 (m, 1H), 7.22 (d, J=8.1 Hz, 2H), 7.66-7.72 (m, 2H); 8.19 (d, J=4.7 Hz, 1H) Anal. C20H20N2O4, Mol. Wt.: 352.38. Found: ESI-MS: 352.9 (M+H)+.

後処理

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-77acb199190646b69d5bf45a17acfef3
出典データセット
uspto-grants-2009_03
特許番号
US07501404B2

反応ノート

読み込み中…