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 2382

反応式

HRID 2382 の反応式
[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]

参加物

3

反応物 1

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

生成物 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-benzenedicarboxamide収率 90.3%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

反応条件

温度
80 °C

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.

後処理

  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

出典と根拠

ORDレコード
ord-07ac67ae638344aebabaeb810563c749
出典データセット
uspto-grants-1998_03
特許番号
US05728877

関連ノート

読み込み中…