Benzyl 6-oxopyran-3-carboxylate → Benzyl 1-(2-(tert-butoxy)-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 509410ノート

反応式

HRID 509410 の反応式
O=[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4][O:3]1.Cl.[C:19]([O:23][C:24](=[O:27])[CH2:25][NH2:26])([CH3:22])([CH3:21])[CH3:20]>CO>[C:19]([O:23][C:24](=[O:27])[CH2:25][N:26]1[C:2](=[O:3])[CH:7]=[CH:6][C:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:4]1)([CH3:22])([CH3:21])[CH3:20]

参加物

4

反応物 2

HCID 325763Benzyl 6-oxopyran-3-carboxylateHCID 2725036Glycine tert-butyl ester hydrochloride

生成物 1

HCID 86687994Benzyl 1-(2-(tert-butoxy)-2-oxoethyl)-6-oxo-1,6-dihydropyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
23 °C

実験手順

A solution of benzyl 2-oxo-2H-pyran-5-carboxylate (906 mg, 3.94 mmol) and glycine tert butyl ester hydrochloride (726 mg, 4.33 mmol) in MeOH (20 mL) was treated with TEA (1.642 mL, 11.81 mmol). The reaction was stirred at 23° C. under nitrogen. After 1 h, the solution was concentrated in vacuo and purified by silica gel chromatography (eluent: 10-50% EtOAc/hexane), affording the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=2.35 Hz, 1H), 7.90 (dd, J=9.59, 2.54 Hz, 1H), 7.31-7.54 (m, 5H), 6.55 (d, J=9.59 Hz, 1H), 5.30 (s, 2H), 4.56 (s, 2H), 1.48 (s, 9H). MS (ESI, positive ion) m/z: 366.0 (M+H).

後処理

  1. concentrationthe solution was concentrated in vacuo
  2. custompurified by silica gel chromatography (eluent: 10-50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-9827ccc80cb0404fb0e5ac857e89e8e7
出典データセット
uspto-grants-2015_08
特許番号
US09096527B2

反応ノート

読み込み中…