Hydrochloric Acid → 5,5'-(2,7-dihydroxyoctane-1,8-diyl)bis(acetylazanediyl)bis(N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-N1,N3-dimethylisophthalamide)

HRID 41832

반응식

HRID 41832 반응식
[OH-:1].[K+].[C:3]([NH:6][C:7]1[C:8]([I:33])=[C:9]([C:24]([N:26]([CH2:28][CH:29]([OH:32])[CH2:30][OH:31])[CH3:27])=[O:25])[C:10]([I:23])=[C:11]([C:21]=1[I:22])[C:12]([N:14]([CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH3:15])=[O:13])(=[O:5])[CH3:4].B(O)(O)O.[O:38]1[CH2:40][CH:39]1[CH2:41][CH2:42][CH2:43][CH2:44][CH:45]1[CH2:47][O:46]1.Cl>C(#N)C.O.O.CO>[OH:38][CH:39]([CH2:41][CH2:42][CH2:43][CH2:44][CH:45]([OH:46])[CH2:47][N:6]([C:7]1[C:21]([I:22])=[C:11]([C:12]([N:14]([CH2:16][CH:17]([OH:20])[CH2:18][OH:19])[CH3:15])=[O:13])[C:10]([I:23])=[C:9]([C:8]=1[I:33])[C:24]([N:26]([CH2:28][CH:29]([OH:32])[CH2:30][OH:31])[CH3:27])=[O:25])[C:3](=[O:1])[CH3:4])[CH2:40][N:6]([C:7]1[C:21]([I:22])=[C:11]([C:12]([N:14]([CH3:15])[CH2:16][CH:17]([OH:20])[CH2:18][OH:19])=[O:13])[C:10]([I:23])=[C:9]([C:8]=1[I:33])[C:24]([N:26]([CH3:27])[CH2:28][CH:29]([OH:32])[CH2:30][OH:31])=[O:25])[C:3](=[O:5])[CH3:4]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 7628Boric AcidHCID 14797Potassium HydroxideHCID 170481,2:7,8-DiepoxyoctaneHCID 198101Compound 17

생성물 1

HCID 442189505,5'-(2,7-dihydroxyoctane-1,8-diyl)bis(acetylazanediyl)bis(N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-N1,N3-dimethylisophthalamide)

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 22242641Methanol--water (1/1)용매

실험 절차

To a stirred solution of water/methanol (4.9 ml, 2.5 ml) and potassium hydroxide (0.47 g, 8.4 mmol) at 40° C. was added 5-acetylamino-N,N′-bis-(2,3-dihydroxypropyl)-2,4,6-triiodo-N,N′-dimethyl isophthalamide (5.0 g, 6.5 mmol). To the clear solution was then added boric acid (0.28 g, 4.5 mmol). The mixture was cooled to room temperature and pH adjusted to 12.6. 2-(4-oxiran-2-ylbutyl)oxirane (0.315 g, 2.22 mmol) was added. The pH of the solution was adjusted to the interval 12.6-13. The reaction was left over weekend. To the solution was added HCl (18%) to pH 4. Salts were removed by treatment with ion exchanger AMB200C and IRA67. The solution was filtered from the resin and evaporated. An aliquot of the crude material was purified by preparative HPLC (column Phenomenex Luna C18(2) 10 μm 250×50.0 mm, solvents: A=water and B=acetonitrile; gradient 10-18% B over 60 min; flow 50.0 ml/min, UV detection at 214 nm and 254 nm), the product was obtained in 393 mg after lyophilisation. Analysis by LC-MS (column Agilent Zorbax SB-Aq 3.5 μm 3.0×100 mm, solvents: A=water/0.1% formic acid and B=acetonitrile/0.1% formic acid; gradient 0-30% B over 20 min; flow 0.3 ml/min, UV detection at 214 and 254 nm, ESI-MS) gave one broad peak centred at 14.77 minutes with m/z 1692.6 (MH+) corresponding to the structure.

후처리

  1. waitThe reaction was left over weekend
  2. customSalts were removed by treatment with ion exchanger AMB200C and IRA67
  3. filtrationThe solution was filtered from the resin
  4. customevaporated
  5. customAn aliquot of the crude material was purified by preparative HPLC (column Phenomenex Luna C18(2) 10 μm 250×50.0 mm, solvents
  6. customwas obtained in 393 mg after lyophilisation
  7. waitgradient 0-30% B over 20 min
  8. customgave one broad peak centred at 14.77 minutes with m/z 1692.6 (MH+) corresponding to the structure

출처 및 근거

ORD 기록
ord-95741dc61980472eada5cd8c0a4107e5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08535642B2

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