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

HRID 1189566

反応式

HRID 1189566 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

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).

後処理

  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%

出典と根拠

ORDレコード
ord-4c56fd6723294eeaa82c4d7ea72fdf85
出典データセット
uspto-grants-2014_03
特許番号
US08674115B2

関連ノート

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