Sodium Bicarbonate → ethyl 2-(2-methyl-6,7-dihydropyrano[4,3-b]pyrrol-1(4H)-yl)acetate

HRID 1189566

반응식

HRID 1189566 반응식
O=[C:2]([CH3:11])[CH2:3][CH:4]1[C:9](=O)[CH2:8][CH2:7][O:6][CH2:5]1.Cl.[NH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:11][C:2]1[N:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]2[CH2:8][CH2:7][O:6][CH2:5][C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 583109733-(2-Oxopropyl)tetrahydro-4H-pyran-4-one

생성물 1

HCID 58310957ethyl 2-(2-methyl-6,7-dihydropyrano[4,3-b]pyrrol-1(4H)-yl)acetate수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
25 °C

실험 절차

3-(2-oxopropyl)dihydro-2H-pyran-4(3H)-one (0.41 g, 2.63 mmol) in dichloromethane (3 ml) was stirred at room temperature, and ethyl 2-aminoacetate hydrochloride (0.366 g, 2.63 mmol) was added, followed by sodium bicarbonate (0.441 g, 5.25 mmol). The resulting mixture was stirred at 25° C. for 15 hours, after which TLC showed that the reaction was complete. DCM was added, the organic layer was separated, washed with water, brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel using an automated Biotage system, EtOAc/Hexane 5-30%, to give the desired product (0.41 g, yield 70%). 1H NMR (400 MHz, CDCl3) δ (ppm) 5.69 (s, 1H), 4.62 (s, 2H), 4.44 (s, 2H), 4.21 (q, 2H), 3.95-3.94 (m, 2H), 2.58-2.55 (m, 2H), 2.18 (s, 3H), 1.28 (t, 2H).

후처리

  1. customthe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel using an automated Biotage system, EtOAc/Hexane 5-30%

출처 및 근거

ORD 기록
ord-4c56fd6723294eeaa82c4d7ea72fdf85
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674115B2

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