Hydrochloric Acid → 5.5'-(2,3-dihydroxybutane-1,4-diyl)bis(formylazanediyl)bis(N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)

HRID 1408283

反応式

HRID 1408283 の反応式
[OH-:1].[K+].[OH:3][CH:4]([CH2:29][OH:30])[CH2:5][NH:6][C:7](=[O:28])[C:8]1[C:21]([I:22])=[C:20]([NH:23][CH:24]=[O:25])[C:19]([I:26])=[C:10]([C:11]([NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])=[O:12])[C:9]=1[I:27].B(O)(O)O.[CH2:35]1[O:37][CH:36]1[CH:38]1[O:40][CH2:39]1.Cl>CO.O>[OH:40][CH:38]([CH:36]([OH:37])[CH2:35][N:23]([C:20]1[C:21]([I:22])=[C:8]([C:7]([NH:6][CH2:5][CH:4]([OH:3])[CH2:29][OH:30])=[O:28])[C:9]([I:27])=[C:10]([C:19]=1[I:26])[C:11]([NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])=[O:12])[CH:24]=[O:1])[CH2:39][N:23]([C:20]1[C:19]([I:26])=[C:10]([C:11]([NH:13][CH2:14][CH:15]([OH:18])[CH2:16][OH:17])=[O:12])[C:9]([I:27])=[C:8]([C:21]=1[I:22])[C:7]([NH:6][CH2:5][CH:4]([OH:3])[CH2:29][OH:30])=[O:28])[CH:24]=[O:25]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 7628Boric Acid2 回HCID 11254DiepoxybutaneHCID 14797Potassium Hydroxide2 回HCID 86649138N1,N3-bis(2,3-dihydroxypropyl)-5-formylamino-2,4,6-triiodoisophthalamide

生成物 1

HCID 252221725.5'-(2,3-dihydroxybutane-1,4-diyl)bis(formylazanediyl)bis(N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)収率 43%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a stirred solution of water (10 ml), methanol (5 ml) and potassium hydroxide (1.0 g, 16.4 mmol) was added N1,N3-bis(2,3-dihydroxypropyl)-5-formylamino-2,4,6-triiodoisophthalamide (Example 1a) (10.0 g, 13.6 mmol). To the clear solution was then added boric acid (0.59 g, 9.5 mmol). The pH was continuously maintained at pH 12.6 by addition of potassium hydroxide (10 M) and 1,3-butadiene diepoxide (0.40 g, 4.7 mmol) was added. The pH of the solution was continuously maintained within the interval from 12.6 to 13 by addition of solid boric acid for 5 hours and then left over the weekend. The solution was neutralized by addition of hydrochloric acid (18% w) and then treated with ion exchangers (AMB200C, 20 ml) and (IRA67, 20 ml). The resins were removed by filtration and rinsed with water and the combined aqueous volume was reduced in vacuo. The crude product was purified by preparative HPLC (column Phenomenex Luna C18 10 μm 250×50.0 mm, solvents: A=water and B=acetonitrile; gradient 0-10% B over 60 min; flow 50.0 ml/ min, UV detection at 214 nm and 254 nm). After freeze drying 3.1 g 5.5′-(2,3-dihydroxybutane-1,4-diyl)bis(formylazanediyl)bis(N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide) (43% yield) was obtained.

後処理

  1. additionwas added
  2. waitleft over the weekend
  3. additiontreated with ion exchangers (AMB200C, 20 ml) and (IRA67, 20 ml)
  4. customThe resins were removed by filtration
  5. washrinsed with water
  6. customThe crude product was purified by preparative HPLC (column Phenomenex Luna

出典と根拠

ORDレコード
ord-4caf1daa53b54a60bd48eaef394ce998
出典データセット
uspto-grants-2014_12
特許番号
US08920780B2

関連ノート

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