反応 #2478

反応方程式

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

→

desired product

収率 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

収率 90.3%

溶媒

methyl cellosolve

反応条件

後処理

1. 1
   workup.ADDITION1927, 60, 2456) (0.056 mol) are added
2. 2
   その他After removing methyl cellosolve
3. 3
   その他by evaporation under reduced pressure
4. 4
   workup.ADDITIONthe oily residue is treated with CH2Cl2 (2×250 mL)
5. 5
   ろ過The solid, filtered
6. 6
   その他dried
7. 7
   workup.DISSOLUTIONis dissolved in abs
8. 8
   ろ過EtOH (190 mL) and after filtration of sodium p-toluensulfonate
9. 9
   濃縮the solution is concentrated to dryness
10. 10
    その他EtOH (150 mL) and after evaporation the resulting residue
11. 11
    その他is crystallized from abs

実験手順

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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