N,N'-Bis[2,3-bis(acetyloxy)propyl]-5-[4-(R)-(hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide → 2,4,6-Triiodoisophthalamide

To a solution of N,N'-Bis[2,3-bis(acetyloxy)propyl]-5-(4)-(R)-(hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide of Example 2b (0.410 g, 0.51 mmol) in anhydrous methanol (7 ml) was added a methanolic solution of sodium methoxide (1.18 ml, 1M solution) and the mixture was stirred at room temperature for 1 h. The methanol was then removed on the rotary evaporator and water (8 ml) was added to redissolve the white residue. Dowex-50 (H+) was added to this solution portionwise to bring the pH down to approximately 7.0. The Dowex-50 resin was filtered off, water was removed on the rotary evaporator, and the white solid dried in vacuo at 60° over P2O5. The solid thus obtained (0.350 g) was redissolved in water (0.5 ml), seeded with a tiny crystal of the racemate and left overnight. The crystallized product was filtered, washed with cold water and dried overnight over P2O5 to obtain N,N'-Bis[2,3-bis(acetyloxy)propyl]-5-(4)-(R)-(hydroxymethyl)-2-oxo-3-oxazolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as white crystalline needles (0.32 g, 84%).

1. customThe methanol was then removed on the rotary evaporator and water (8 ml)
2. additionwas added
3. dissolutionto redissolve the white residue
4. additionDowex-50 (H+) was added to this solution portionwise
5. filtrationThe Dowex-50 resin was filtered off
6. customwater was removed on the rotary evaporator
7. dry with materialthe white solid dried in vacuo at 60° over P2O5
8. customThe solid thus obtained (0.350 g)
9. waitleft overnight
10. filtrationThe crystallized product was filtered
11. washwashed with cold water
12. dry with materialdried overnight over P2O5

ORD record

ord-defed4baeda443be8e0c40e9b4e6ddcf

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05591846