Acetate → N,N'-Bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-5-hydroxyacetamido-2,4,6-triiodoisophthalamide

HRID 1461610

반응식

HRID 1461610 반응식
C([O:4][CH2:5][C:6]([NH:8][C:9]1[C:10]([I:39])=[C:11]([C:28]([NH:30][CH2:31][CH:32]([CH2:34][CH:35]([OH:38])[CH2:36][OH:37])[OH:33])=[O:29])[C:12]([I:27])=[C:13]([C:25]=1[I:26])[C:14]([NH:16][CH2:17][CH:18]([CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[OH:19])=[O:15])=[O:7])(=O)C.C([O-])(=O)C>O.S(=O)(=O)(O)O>[OH:24][CH:21]([CH2:22][OH:23])[CH2:20][CH:18]([OH:19])[CH2:17][NH:16][C:14](=[O:15])[C:13]1[C:25]([I:26])=[C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])[C:10]([I:39])=[C:11]([C:28]([NH:30][CH2:31][CH:32]([CH2:34][CH:35]([OH:38])[CH2:36][OH:37])[OH:33])=[O:29])[C:12]=1[I:27]

참가 물질

5

반응물 2

HCID 175AcetateHCID 867453315-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide

생성물 1

HCID 86745330N,N'-Bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-5-hydroxyacetamido-2,4,6-triiodoisophthalamide수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

실험 절차

5-Acetoxyacetamido-N,N'-bis[(2,3-dihydroxypropyl)-2-hydroxyethyl]-2,4,6-triiodoisophthalamide (77 g, 0.086 g-mole) is dissolved in 270 ml of hot water containing 8.2 g (0.08 g-mole) sulfuric acid. The solution is stirred and heated at 95°-100° C. to hydrolyze the acetate. At the end of the reaction, the solution is cooled to room temperature and deionized using an anionic exchange resin, IRA-93 (Rohm and Haas Co.) to remove sulfuric acid. The solution is then concentrated and the crude product is purified by preparative liquid chromatography to provide the purified desired product (51 g; 0.06 g-mole, 70% yield). The 13C nmr spectra are consistent with the structure. The HPLC purity is 99.1% (C18, H2O/MeOH; 95/5). The water solubility (w/v) is 100%; the iv LD50 in mice is 5 g I/kg (based on iodine content). Osmolality: 676 mOsm/kg (32% I); viscosity: 8.2 cps (37°), 10.0 cps (25 °) (32% I).

후처리

  1. temperatureheated at 95°-100° C.
  2. customAt the end of the reaction
  3. customto remove sulfuric acid
  4. concentrationThe solution is then concentrated
  5. customthe crude product is purified by preparative liquid chromatography
  6. customto provide the

출처 및 근거

ORD 기록
ord-3e5d0ed483124381885cc3fbfb12fcee
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075502

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