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

HRID 1783428노트

반응식

HRID 1783428 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-77acb199190646b69d5bf45a17acfef3
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501404B2

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