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

HRID 963773

반응식

HRID 963773 반응식
[Na].[OH:2][CH2:3][CH:4]([NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([OH:17])[C:13]([I:18])=[C:12]([C:19]([NH:21][CH:22]([CH2:25][OH:26])[CH2:23][OH:24])=[O:20])[C:11]=1[I:27])=[O:9])[CH2:5][OH:6]>COCCO>[NH2:7][C:8](=[O:9])[C@H:10]([CH3:11])[O:17][C:14]1[C:15]([I:16])=[C:10]([C:8]([NH:7][CH:4]([CH2:5][OH:6])[CH2:3][OH:2])=[O:9])[C:11]([I:27])=[C:12]([C:19]([NH:21][CH:22]([CH2:25][OH:26])[CH2:23][OH:24])=[O:20])[C:13]=1[I:18]

참가 물질

3

반응물 1

HCID 88296896N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-hydroxy-2,4,6-triiodo-1,3-benzenedicarboxamide sodium salt

생성물 1

HCID 11029100(S)-5-(2-amino-1-methyl-2-oxoethoxy)-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide수율 90.3%

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매

반응 조건

온도
80 °C

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.

후처리

  1. addition1927, 60, 2456) (0.056 mol) are added
  2. customAfter removing methyl cellosolve
  3. customby evaporation under reduced pressure
  4. additionthe oily residue is treated with CH2Cl2 (2×250 mL)
  5. filtrationThe solid, filtered
  6. customdried
  7. dissolutionis dissolved in abs
  8. filtrationEtOH (190 mL) and after filtration of sodium p-toluensulfonate
  9. concentrationthe solution is concentrated to dryness
  10. customEtOH (150 mL) and after evaporation the resulting residue
  11. customis crystallized from abs

출처 및 근거

ORD 기록
ord-a4849b204efb4893b6929f512ea946a9
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763663

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