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

HRID 383015ノート

反応式

HRID 383015 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-614af82f3bca40538fefa3baa5e47547
出典データセット
uspto-grants-2001_10
特許番号
US06310243B1

反応ノート

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