Sodium Hydroxide → 10-(2,3,4-Trihydroxybutyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane

HRID 23856

反応式

HRID 23856 の反応式
[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2].[OH-].[Na+].CC1(C)[O:32][CH:31]([CH:33]2[O:35][CH2:34]2)[CH2:30][O:29]1>O.O1CCOCC1>[OH:35][CH:33]([CH:31]([OH:32])[CH2:30][OH:29])[CH2:34][N:14]1[CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH2:21][C:22]([OH:24])=[O:23])[CH2:7][CH2:6][N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:16][CH2:15]1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 1078301,4,7-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododecaneHCID 131868272,2-Dimethyl-4-(oxiran-2-YL)-1,3-dioxolane

生成物 1

HCID 1069484210-(2,3,4-Trihydroxybutyl)-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

10.0 g (28.87 mmol) of 1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane (DO3A) is dissolved in 40 ml of water, and the pH is set at 13 with 5N sodium hydroxide solution. A solution of 6.24 g (43.30 mmol) of 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethylene oxide (DE 3,150,917) in 10 ml of dioxane is added thereto, and the mixture is stirred for 24 hours at room temperature. The mixture is diluted with 60 ml of water and extracted three times with 50 ml of ether. The aqueous phase is brought to pH 2 with 10% strength hydrochloric acid and evaporated. The residue is dissolved in a small amount of water and passed to a cation exchange column (IR 120). After flushing with water, the ligand is eluted with 0.5-normal aqueous ammonia solution. The fractions are evaporated, the ammonium salt is taken up in a small amount of water and passed over an anion exchange column (IRA 67). The mixture is first washed with water and then eluted with 0.5-normal aqueous formic acid. The product is evaporated under vacuum, the residue is dissolved in a small amount of hot methanol, and acetone is added, thus crystallizing the title compound.

後処理

  1. extractionextracted three times with 50 ml of ether
  2. customevaporated
  3. dissolutionThe residue is dissolved in a small amount of water
  4. customAfter flushing with water
  5. washthe ligand is eluted with 0.5-normal aqueous ammonia solution
  6. customThe fractions are evaporated
  7. washThe mixture is first washed with water
  8. washeluted with 0.5-normal aqueous formic acid
  9. customThe product is evaporated under vacuum
  10. dissolutionthe residue is dissolved in a small amount of hot methanol, and acetone
  11. additionis added
  12. customthus crystallizing the title compound

出典と根拠

ORDレコード
ord-5aa4b7ab51f544538ba3ea3976339c5c
出典データセット
uspto-grants-2005_02
特許番号
US06855309B2

関連ノート

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