Trimethylolethane → Acetic acid 2-acetoxy-3-[3-{2-[3,5-bis-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-phenylcarbamoyloxymethyl]-3-hydroxy-2-methyl-propoxycarbonylamino}-5-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-benzoylamino]propyl ester

HRID 1038276Notes

Reaction equation

HRID 1038276 reaction equation
[C:1]([O:4][CH2:5][CH:6]([O:37][C:38](=[O:40])[CH3:39])[CH2:7][NH:8][C:9](=[O:36])[C:10]1[C:15]([I:16])=[C:14]([N:17]=[C:18]=[O:19])[C:13]([I:20])=[C:12]([C:21](=[O:34])[NH:22][CH2:23][CH:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:25][O:26][C:27](=[O:29])[CH3:28])[C:11]=1[I:35])(=[O:3])[CH3:2].[OH:41][CH2:42][C:43]([CH2:47][OH:48])([CH2:45][OH:46])[CH3:44]>ClCCl>[C:31]([O:30][CH:24]([CH2:23][NH:22][C:21](=[O:34])[C:12]1[C:11]([I:35])=[C:10]([C:9](=[O:36])[NH:8][CH2:7][CH:6]([O:37][C:38](=[O:40])[CH3:39])[CH2:5][O:4][C:1](=[O:3])[CH3:2])[C:15]([I:16])=[C:14]([NH:17][C:18]([O:41][CH2:42][C:43]([CH2:47][O:48][C:18](=[O:19])[NH:17][C:14]2[C:13]([I:20])=[C:12]([C:21](=[O:34])[NH:22][CH2:23][CH:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:25][O:26][C:27](=[O:29])[CH3:28])[C:11]([I:35])=[C:10]([C:9](=[O:36])[NH:8][CH2:7][CH:6]([O:37][C:38](=[O:40])[CH3:39])[CH2:5][O:4][C:1](=[O:3])[CH3:2])[C:15]=2[I:16])([CH3:44])[CH2:45][OH:46])=[O:19])[C:13]=1[I:20])[CH2:25][O:26][C:27](=[O:29])[CH3:28])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 6502TrimethylolethaneHCID 10463456Acetic acid 1-acetoxymethyl-2-[3-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-5-isocyanato-benzoylamino]-ethyl ester

Product 1

HCID 86646402Acetic acid 2-acetoxy-3-[3-{2-[3,5-bis-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-phenylcarbamoyloxymethyl]-3-hydroxy-2-methyl-propoxycarbonylamino}-5-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-benzoylamino]propyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetic acid 1-acetoxymethyl-2-[3-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-5-isocyanato-benzoylamino]-ethyl ester in dichloromethane was added 1,1,1-tris(hydroxymethyl)ethane (0.3 equivalent). The reaction mixture was stirred for 18 hours and then purified by column chromatography to give acetic acid 2-acetoxy-3-[3-{2-[3,5-bis-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-phenylcarbamoyloxymethyl]-3-hydroxy-2-methyl-propoxycarbonylamino}-5-(2,3-diacetoxy-propylcarbamoyl)-2,4,6-triiodo-benzoylamino]propyl ester. This was dissolved in methanol and treated with aquesous ammonia. The material was purified by preparatie HPLC to give 1,3-bis-[N,N′-Bis-(2,3-dihydroxy-propyl)-2,4,6-triiodo-5-carbamido-isophthalamide]-2-methyl-2-hydroxymethylpropane as a white powder after freeze drying.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-68d50acb249c4613b0d723f2403fe327
Source dataset
uspto-grants-2013_10
Patent number
US08551449B2

Reaction notes

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