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

반응식

HRID 1408283 반응식
[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]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 7628Boric Acid2회HCID 11254DiepoxybutaneHCID 14797Potassium Hydroxide2회HCID 86649138N1,N3-bis(2,3-dihydroxypropyl)-5-formylamino-2,4,6-triiodoisophthalamide

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4caf1daa53b54a60bd48eaef394ce998
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08920780B2

연결된 노트

불러오는 중…