Reaction #2275692

ord-576c6e2b17d44d1f934487b0306a2be3

Reaction equation

CC(=O)OCC(=O)Nc1c(I)c(C(=O)NCC(O)CN(C(C)=O)c2c(I)c(C(=O)NCC3COC(C)(C)O3)c(I)c(C(=O)NCC3COC(C)(C)O3)c2I)c(I)c(C(=O)NCC2COC(C)(C)O2)c1I
Acetic acid {3-[3-(acetyl-{3,5-bis-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenyl}-amino)-2-hydroxy-propylcarbamoyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester
→
CC(=O)N(CC(O)CNC(=O)c1c(I)c(NCO)c(I)c(C(=O)NCC(O)CO)c1I)c1c(I)c(C(=O)NCC(O)CO)c(I)c(C(=O)NCC(O)CO)c1I
desired product
CC(=O)N(CC(O)CNC(=O)c1c(I)c(NCO)c(I)c(C(=O)NCC(O)CO)c1I)c1c(I)c(C(=O)NCC(O)CO)c(I)c(C(=O)NCC(O)CO)c1I
5{[3-(3-Hydroxymethylamino-5-[(2,3-dihydroxypropyl)aminocarbonyl]-2,4,6-triiodobenzoylamino)-2-hydroxypropyl]-acetyl-amino}-N,N′-bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-isophthalamide

Reactants

CC(=O)OCC(=O)Nc1c(I)c(C(=O)NCC(O)CN(C(C)=O)c2c(I)c(C(=O)NCC3COC(C)(C)O3)c(I)c(C(=O)NCC3COC(C)(C)O3)c2I)c(I)c(C(=O)NCC2COC(C)(C)O2)c1I
Acetic acid {3-[3-(acetyl-{3,5-bis-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenyl}-amino)-2-hydroxy-propylcarbamoyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester

Reagents

None

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction was then concentrated to dryness
  2. 2
    Otherthe crude material purified by R-HPLC

Procedure

Acetic acid {3-[3-(acetyl-{3,5-bis-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenyl}-amino)-2-hydroxy-propylcarbamoyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester (1.2 g, 725 μmol) was refluxed in MeOH/2M HCl (1:1, 5 mL:5 mL) for 1 hour. The reaction was then concentrated to dryness and the crude material purified by R-HPLC to give the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08323619B2uspto-grants-2012_12