Iodine → 5-(N-(3-(N-(3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodophenyl)acetamido)-2-hydroxypropyl)formamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

HRID 1408287

Reaktionsgleichung

Reaktionsgleichung von HRID 1408287
[CH2:1]([N:4]([C:8]1[C:9]([I:32])=[C:10]([C:24]([NH:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30])=[O:25])[C:11]([I:23])=[C:12]([C:21]=1[I:22])[C:13]([NH:15][CH2:16][CH:17]([OH:20])[CH2:18][OH:19])=[O:14])[C:5](=[O:7])[CH3:6])[CH:2]=[CH2:3].[I-].[K+].II.[OH:37][CH:38]([CH2:63][OH:64])[CH2:39][NH:40][C:41](=[O:62])[C:42]1[C:55]([I:56])=[C:54]([NH:57][CH:58]=[O:59])[C:53]([I:60])=[C:44]([C:45]([NH:47][CH2:48][CH:49]([OH:52])[CH2:50][OH:51])=[O:46])[C:43]=1[I:61].[OH-:65].[K+]>O.CO>[OH:20][CH:17]([CH2:18][OH:19])[CH2:16][NH:15][C:13]([C:12]1[C:21]([I:22])=[C:8]([N:4]([CH2:1][CH:2]([OH:65])[CH2:3][N:57]([C:54]2[C:53]([I:60])=[C:44]([C:45]([NH:47][CH2:48][CH:49]([OH:52])[CH2:50][OH:51])=[O:46])[C:43]([I:61])=[C:42]([C:55]=2[I:56])[C:41]([NH:40][CH2:39][CH:38]([OH:37])[CH2:63][OH:64])=[O:62])[CH:58]=[O:59])[C:5](=[O:7])[CH3:6])[C:9]([I:32])=[C:10]([C:24](=[O:25])[NH:26][CH2:27][CH:28]([OH:31])[CH2:29][OH:30])[C:11]=1[I:23])=[O:14]

Komponenten

8

Edukt 5

HCID 807IodineHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 596228935-(N-allylacetamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamideHCID 86649138N1,N3-bis(2,3-dihydroxypropyl)-5-formylamino-2,4,6-triiodoisophthalamide

Produkt 1

HCID 468316225-(N-(3-(N-(3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodophenyl)acetamido)-2-hydroxypropyl)formamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a stirred solution of water (10 ml) and methanol (7 ml) is added 5-(N-allylacetamido)-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide (5.0 g 6.35 mmol). pH is adjusted to pH 2 and a solution of potassium iodide (1.05 g, 6.35 mmol) and iodine 1.61 g, 6.35 mmol) in water (5 ml) and methanol (5 ml) is added drop wise at 50° C. The mixture is stirred over night. The solution is cooled to 10° C. and N,N′-Bis-(2,3-dihydroxy-propyl)-5-formylamino-2,4,6-triiodo-isophthalamide (Example 1a)(4.65 g 6.35 mmol) is added. Potassium hydroxide (10 M) is added drop wise to maintain a stable pH of 11.6 and the mixture is stirred for 24 hours. The solution is diluted with water (50 ml) and treated with ion exchangers (AMB200C, 20 ml) and (IRA67, 20 ml). The resins are filtered off and rinsed with water. The combined aqueous phases are reduced in vacuo and the crude product is 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.

Aufarbeitung

  1. temperatureto maintain a stable pH of 11.6
  2. stirringthe mixture is stirred for 24 hours
  3. additiontreated with ion exchangers (AMB200C, 20 ml) and (IRA67, 20 ml)
  4. filtrationThe resins are filtered off
  5. washrinsed with water
  6. customthe crude product is purified by preparative HPLC (column Phenomenex Luna

Quellen und Nachweise

ORD-Eintrag
ord-d4231570eb3b400fbdcef0ad3d6fdb5e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08920780B2

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