Ethyl 4,6-diiodo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate → 3-(2-carboxyethyl)-4,6-diiodo-1H-indole-2-carboxylic acid

HRID 467426ノート

反応式

HRID 467426 の反応式
[I:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:7]2[C:3]=1[C:4]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[C:5]([C:12]([O:14]CC)=[O:13])[NH:6]2.O.O.O.[OH-].[Li+]>O1CCCC1.O>[C:19]([CH2:18][CH2:17][C:4]1[C:3]2[C:7](=[CH:8][C:9]([I:11])=[CH:10][C:2]=2[I:1])[NH:6][C:5]=1[C:12]([OH:14])=[O:13])([OH:21])=[O:20]

参加物

5

反応物 2

HCID 71281158Ethyl 4,6-diiodo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylateHCID 86677587Lithium hydroxide trihydrate

生成物 1

HCID 712809393-(2-carboxyethyl)-4,6-diiodo-1H-indole-2-carboxylic acid収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Ethyl 4,6-diiodo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (1.71 g, 5 mmol) was dissolved in 15 ml tetrahydrofurane (THF) with stirring at rt. Then a solution of 0.63 g of lithium hydroxide trihydrate (3 equiv.) in 15 ml water was added and the resulting mixture was let to stir at rt for 24 h. After completion of the reaction THF was removed under reduced pressure and the pH was adjusted to 4-5, and the product was extracted with diethyl ether (3×15 ml). The organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to yield a light-beige-colored solid in 95-100% yield. mp. 280-282° C. 1H-NMR (DMSO-d6) δ 2.48 (m, 2H, 2′-H); 3.49 (m, 2H, 1′-H); 7.78 (dd, 2H, J=1.7 Hz, 5-H, 7-H); 11.80 (s, 1H, NH); 12.68 (b, 2H, 2CO2H). 13C-NMR (DMSO-d6) δ 18.9 (C-2′); 36.4 (C-1′), 88.3 (C-4); 89.5 (C-6); 121.4 (C-7); 122.0 (C-3); 126.2 (C-2); 126.4 (C-3a); 137.8 (C-7a); 138.1 (C7); 162.7 (2′-CO2H); 173.58 (2-CO2H). LC-MS (m/z): 503 [M+NH4+]+, 486 [M]+, 484 [M]−. Purity (LC-MS): 98%.

後処理

  1. stirringto stir at rt for 24 h
  2. customwas removed under reduced pressure
  3. extractionthe product was extracted with diethyl ether (3×15 ml)
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield a light-beige-colored solid in 95-100% yield

出典と根拠

ORDレコード
ord-069781a446f44796a2d5b0cd785e7909
出典データセット
uspto-grants-2014_01
特許番号
US08623593B1

反応ノート

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