반응 #2478

반응 방정식

N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-hydroxy-2,4,6-triiodo-1,3-benzenedicarboxamide sodium salt

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desired product

수율 90.3%

(S)-5-(2-amino-1-methyl-2-oxoethoxy)-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

수율 90.3%

용매

methyl cellosolve

반응 조건

후처리

1. 1
   workup.ADDITION1927, 60, 2456) (0.056 mol) are added
2. 2
   기타After removing methyl cellosolve
3. 3
   기타by evaporation under reduced pressure
4. 4
   workup.ADDITIONthe oily residue is treated with CH2Cl2 (2×250 mL)
5. 5
   여과The solid, filtered
6. 6
   기타dried
7. 7
   workup.DISSOLUTIONis dissolved in abs
8. 8
   여과EtOH (190 mL) and after filtration of sodium p-toluensulfonate
9. 9
   농축the solution is concentrated to dryness
10. 10
    기타EtOH (150 mL) and after evaporation the resulting residue
11. 11
    기타is crystallized from abs

실험 절차

To a solution of 21.8 g of N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-hydroxy-2,4,6-triiodo-1,3-benzenedicarboxamide sodium salt (prepared according to the procedure described in patent EP 185130) (0.03 mol) in 70 mL of methyl cellosolve, heated to 80° C., 14.6 g of R-2-[[(4-methylphenyl)sulfonyl]oxy]propanamide (prepared according to the procedure described in Markert, F. Chem. Ber. 1927, 60, 2456) (0.056 mol) are added and the resulting mixture is kept under stirring in the same conditions for 8 h. After removing methyl cellosolve by evaporation under reduced pressure, the oily residue is treated with CH2Cl2 (2×250 mL). The solid, filtered and dried is dissolved in abs. EtOH (190 mL) and after filtration of sodium p-toluensulfonate, the solution is concentrated to dryness. The treatment is repeated with abs. EtOH (150 mL) and after evaporation the resulting residue is crystallized from abs. EtOH (75 mL). 10.5 g of the desired product (0.0135 mol) are recovered.

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