Ethanol → HCID 57738870、化合物

HRID 1715734ノート

反応式

HRID 1715734 の反応式
C(O)C.[Na].[N:5]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:24](OCC)(=[O:30])[C:25](OCC)=[O:26]>C(O)(=O)C.O>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][N:5]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:25]([OH:26])[C:24]([OH:30])=[C:6]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:17]

参加物

7

反応物 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 608668Glycine, N,N-bis(2-ethoxy-2-oxoethyl)-, ethyl esterHCID 5360545Sodium2 回

生成物 1

HCID 57738870HCID 57738870、化合物収率 89%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a 1000-mL round bottom flask was added containing a stir bar, and argon atmosphere, and outfitted with a reflux condenser was added ethanol (200 proof, 500 mL) and sodium metal (21.31 g, 927 mmol). When the sodium was completely dissolved, a mixture of triethyl nitrilotriacetate (56.20 g, 204 mmol) and diethyl oxalate (29.44 g, 204 mmol) was added. The mixture was refluxed overnight, whereupon it became a clear, gelatinous solution. After cooling to room temperature, the mixture was poured into 1200 mL of DI water, chilled in an ice bath and acidified with glacial acetic acid (200 mL). The resulting white precipitate was isolated via vacuum filtration and washed with several portions of DI water to yield 59.75 g (89%) of a white solid. mp 121.3-121.8° C.; 1H NMR (300 MHz, CDCl3): δ 7.51 (s, 2H), 5.32 (s, 2H), 4.39 (q, 4H, J=7.7 Hz), 4.20 (q, 2H, J=7.7 Hz), 1.38 (t, 6H, J=7.7 Hz), 1.27 (t, 3H, J=7.7 Hz); 13C NMR (75 MHz, CDCl3): δ 169.5, 162.4, 139.6, 111.1, 61.6, 47.9, 14.5, 14.4; HRMS (EI): Calcd for C14H19NO8 ([M]+), 329.1111, found m/z, 329.1111; Anal. Calcd for C14H19NO8: C, 51.06; H, 5.82; N, 4.25%, found: C, 50.79; H, 5.83; N, 4.22%.

後処理

  1. additionTo a 1000-mL round bottom flask was added
  2. additioncontaining a stir bar
  3. customargon atmosphere, and outfitted with a reflux condenser
  4. additionwas added
  5. temperatureThe mixture was refluxed overnight, whereupon it
  6. temperaturechilled in an ice bath
  7. customThe resulting white precipitate was isolated via vacuum filtration
  8. washwashed with several portions of DI water

出典と根拠

ORDレコード
ord-16c7c62c802f4c81b5460475c5616712
出典データセット
uspto-grants-2010_09
特許番号
US07799932B2

反応ノート

読み込み中…