تفاعل #2478

معادلة التفاعل

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

المردود 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

المردود 90.3%

المذيبات

methyl cellosolve

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر