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

반응식

HRID 1408287 반응식
[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]

참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매3회

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d4231570eb3b400fbdcef0ad3d6fdb5e
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08920780B2

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