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

HRID 509410노트

반응식

HRID 509410 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
23 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9827ccc80cb0404fb0e5ac857e89e8e7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096527B2

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