Diethyl Ether → N,N'-Bis(2,3-dihydroxypropionyl)-N-(2-hydroxyethyl)-3,5-diamino-2,4,6-triiodobenzylalcohol

HRID 1418271ノート

反応式

HRID 1418271 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].[Cs+].[Cs+].[C:41](OCCBr)(=[O:43])[CH3:42].CCOCC>CC(N(C)C)=O.CS(C)=O>[OH:26][CH:25]([CH2:29][OH:28])[C:23]([N:22]([CH2:42][CH2:41][OH:43])[C:19]1[C:18]([I:32])=[C:12]([C:11]([I:33])=[C:10]([NH:9][C:7](=[O:8])[CH:5]([OH:6])[CH2:4][OH:3])[C:20]=1[I:21])[CH2:13][OH:36])=[O:24]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 18429246N,N'-Bis(2,2-dimethyl-1,3-dioxolane-4-carbonyl)-3,5-diamino-2,4,6-triiodobenzylacetate

生成物 1

HCID 18429366N,N'-Bis(2,3-dihydroxypropionyl)-N-(2-hydroxyethyl)-3,5-diamino-2,4,6-triiodobenzylalcohol収率 30%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 31374Dimethylacetamide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 (4 ml) and DMSO (2.5 ml) containing Cs2CO3 (650 mg, 2.0 mmol) and 2-bromoethyl acetate (0.035 ml, 0.31 mmol). After stirring for 1 week, ether (150 ml) and a NaH2PO4 buffer (100 ml) were added, the organic phase was separated and the aqueous phase was extracted with ether (150 ml). The combined organic phases were then washed with water (6×100 ml), dried (Na2SO4) and evaporated. The residue was dissolved in a mixture of methanol (20 ml) and water (20 ml) and pH was adjusted to 12 with aqueous NaOH. After stirring for 1 h, the pH was adjusted to 1.5 with concentrated HCl and stirred for another 16 h. The solution was neutralized with aqueous NaH2PO4 and the solvents were evaporated. Preparative HPLC gave 55 mg (30%) of the pure product.

後処理

  1. customthe organic phase was separated
  2. extractionthe aqueous phase was extracted with ether (150 ml)
  3. washThe combined organic phases were then washed with water (6×100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. dissolutionThe residue was dissolved in a mixture of methanol (20 ml) and water (20 ml) and pH
  7. stirringAfter stirring for 1 h
  8. stirringstirred for another 16 h
  9. customthe solvents were evaporated

出典と根拠

ORDレコード
ord-fc1f1ebcfbcf4a93a5c93645b001e27c
出典データセット
uspto-grants-1999_03
特許番号
US05882628

反応ノート

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