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

HRID 1604154노트

반응식

HRID 1604154 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].[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 31374Dimethylacetamide용매

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 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-c730553ebed4444bac857e825d3dd89b
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05993780

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