1,3-Propanediol → HCID 86646405, compound

HRID 1038278Notes

Reaction equation

HRID 1038278 reaction equation
[CH2:1]([N:4]([CH3:26])[C:5](=[O:25])[C:6]1[C:18]([I:19])=[C:17]([N:20]=[C:21]=[O:22])[C:16]([I:23])=[C:8]([C:9]([N:11]([CH2:13][CH:14]=[CH2:15])[CH3:12])=[O:10])[C:7]=1[I:24])[CH:2]=[CH2:3].[CH2:27]([OH:31])[CH2:28][CH2:29][OH:30]>ClCCl>[CH2:13]([N:11]([CH3:12])[C:9]([C:8]1[C:16]([I:23])=[C:17]([NH:20][C:21]([O:30][CH2:29][CH2:28][CH2:27][O:31][C:21](=[O:22])[NH:20][C:17]2[C:16]([I:23])=[C:8]([C:9](=[O:10])[N:11]([CH2:13][CH:14]=[CH2:15])[CH3:12])[C:7]([I:24])=[C:6]([C:5](=[O:25])[N:4]([CH2:1][CH:2]=[CH2:3])[CH3:26])[C:18]=2[I:19])=[O:22])[C:18]([I:19])=[C:6]([C:5](=[O:25])[N:4]([CH2:1][CH:2]=[CH2:3])[CH3:26])[C:7]=1[I:24])=[O:10])[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 104421,3-PropanediolHCID 57703472HCID 57703472, compound

Product 1

HCID 86646405HCID 86646405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N,N′-Diallyl-2,4,6-triiodo-5-isocyanato-N,N′-dimethyl-isophthalamide in dichloromethane was added 1,3-propane diol (0.5 equivalent). The reaction mixture was stirred for 18 hours and then purified by column chromatography to give) [3,5-Bis-(allyl-methyl-carbamoyl)-2,4,6-triiodo-phenyl]-carbamic acid 3-[3,5-bis-(allyl-methyl-carbamoyl)-2,4,6-triiodo-phenyl]carbamoyloxy-propyl ester. A cis-dihydroxylation using OsO4 and NMMO was performed and the crude mixture was purified by preparative HPLC to give {3,5-Bis-[bis-(2,3-dihydroxy-propyl)-carbamoyl]-2,4,6-triiodo-phenyl}-carbamic acid 3-{3,5-Bis-[bis-(2,3-dihydroxy-propyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyloxy}propyl ester as a white powder after freeze drying.

Workup

  1. custompurified by column chromatography

Sources & evidence

ORD record
ord-abb18b3982d341e5a871017e707b7953
Source dataset
uspto-grants-2013_10
Patent number
US08551449B2

Reaction notes

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