Potassium Carbonate → N,N'-Bis(2,3-dihydroxypropionyl)-N,N'-bis(2-hydroxyethyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

HRID 383015노트

반응식

HRID 383015 반응식
CC1(C)[O:6][CH:5]([C:7]([NH:9][C:10]2[C:11]([I:33])=[C:12]([C:18]([I:32])=[C:19]([NH:22][C:23]([CH:25]3[CH2:29][O:28]C(C)(C)[O:26]3)=[O:24])[C:20]=2[I:21])[CH2:13]CC([O-])=O)=[O:8])[CH2:4][O:3]1.C([O-])([O-])=[O:36].[K+].[K+].C([O:44][CH2:45][CH2:46]Br)(=O)C.[CH3:48][C:49](N(C)C)=[O:50]>CS(C)=O>[OH:6][CH:5]([CH2:4][OH:3])[C:7]([N:9]([CH2:46][CH2:45][OH:44])[C:10]1[C:11]([I:33])=[C:12]([C:18]([I:32])=[C:19]([N:22]([C:23](=[O:24])[CH:25]([OH:26])[CH2:29][OH:28])[CH2:48][CH2:49][OH:50])[C:20]=1[I:21])[CH2:13][OH:36])=[O:8]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 31374DimethylacetamideHCID 18429246N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate

생성물 1

HCID 18362191N,N'-Bis(2,3-dihydroxypropionyl)-N,N'-bis(2-hydroxyethyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

N,N′-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate (204 mg, 0.25 mmol) was dissolved in a mixture of dimethylacetamide (5 ml) and DMSO (1.5 ml) containing K2CO3 (276 mg, 2.0 mmol) and 2-bromoethyl acetate (0.44 ml, 4.0 mmol). After stirring for 48 h, an aqueous NaH2PO4 buffer was added and the mixture was extracted with ether (2×150 ml). The combined organic phases were washed with water (6×100 ml), dried (Na2SO4) and evaporated. The solid residue was dissolved in a mixture of methanol (12 ml) and water (12 ml) and the pH was adjusted to 12 with aqueous NaOH. After stirring for 18 h, the solution was acidified with concentrated HCl (0.70 ml) and stirring was continued for 3 h. The solution was neutralized and the solvents were removed by evaporation. The product was purified by preparative HPLC. Yield: 98 mg (50%).

후처리

  1. extractionthe mixture was extracted with ether (2×150 ml)
  2. washThe combined organic phases were washed with water (6×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. dissolutionThe solid residue was dissolved in a mixture of methanol (12 ml) and water (12 ml)
  6. stirringAfter stirring for 18 h
  7. stirringstirring
  8. waitwas continued for 3 h
  9. customthe solvents were removed by evaporation
  10. customThe product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-614af82f3bca40538fefa3baa5e47547
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310243B1

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